ethyl 4-amino-5-cyanosalicylate

Base Information

• Chemical Name: ethyl 4-amino-5-cyanosalicylate
• CAS No.: 72817-97-1
• Molecular Formula: C10H10 N2 O3
• Molecular Weight: 206.201
• Hs Code.: 2926909090
• European Community (EC) Number: 276-867-6
• DSSTox Substance ID: DTXSID30993613
• Nikkaji Number: J318.839F
• Wikidata: Q82984309
• Mol file: 72817-97-1.mol

Synonyms:Ethyl4-amino-5-cyanosalicylate

Chemical Property of ethyl 4-amino-5-cyanosalicylate

Chemical Property:

• Vapor Pressure: 1.11E-07mmHg at 25°C
• Melting Point: 185-187 °C(Solv: acetic acid (64-19-7))
• Boiling Point: 420.9ºC at 760 mmHg
• PKA: 7.87±0.23(Predicted)
• Flash Point: 208.4ºC
• PSA: 96.34000
• Density: 1.34g/cm3
• LogP: 1.60398
• Storage Temp.: 2-8°C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 206.06914219
• Heavy Atom Count: 15
• Complexity: 284

Purity/Quality:

98%min ^*data from raw suppliers

Ethyl4-Amino-5-cyanosalicylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(C=C(C(=C1)C#N)N)O
• Uses: Ethyl 4-Amino-5-cyanosalicylate is an intermediate in the synthesis of 4-Amino-6-hydroxy-1,3-benzenedicarboxylic Acid (A634570), which is a compound with tuberculostatic activity. It also has antimalarial acitvity.

Technology Process of ethyl 4-amino-5-cyanosalicylate

There total 3 articles about ethyl 4-amino-5-cyanosalicylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 59.0%

(E)-2-(ethoxymethylene)-3-oxobutanoic acid ethyl ester (49836-24-0) + malononitrile (109-77-3) → 4-amino-5-cyano-2-hydroxy-benzoic acid ethyl ester (72817-97-1)

Guidance literature:

malononitrile; With sodium ethanolate; In ethanol; at 4 ℃; for 0.25h;

(E)-2-(ethoxymethylene)-3-oxobutanoic acid ethyl ester; In ethanol; for 1h; Cooling with ice; Reflux;

Reference yield: 39.0%

malononitrile (109-77-3) + 2-ethoxymethylene-3-oxobutanoic acid ethyl ester (3788-94-1) → 4-amino-5-cyano-2-hydroxy-benzoic acid ethyl ester (72817-97-1)

Guidance literature:

malononitrile; With sodium ethanolate; In ethanol; at 20 ℃; for 0.333333h;

2-ethoxymethylene-3-oxobutanoic acid ethyl ester; In ethanol; for 0.5h; Heating;

DOI:10.1021/ol0498848

Reference yield: 29.0%

ethyl acetoacetate (141-97-9) + Ethoxymethylenemalononitrile (123-06-8) → 4-amino-5-cyano-2-hydroxy-benzoic acid ethyl ester (72817-97-1)

Guidance literature:

ethyl acetoacetate; With sodium; In ethanol; water; at 20 ℃; for 0.5h;

Ethoxymethylenemalononitrile; In ethanol; at 80 ℃; for 0.5h;

upstream raw materials:

ethyl acetoacetate

Ethoxymethylenemalononitrile

malononitrile

2-ethoxymethylene-3-oxobutanoic acid ethyl ester

Downstream raw materials:

4-amino-6-hydroxyisophthalic acid

4-Amino-5-cyano-salicylsaeure

4-Amino-5-cyansalicylsaeureamid

4-Amino-5-carbamoylsalicylsaeure-ethylester

Refernces

• 1、 -. "Quinazoline derivative and preparation method and application thereof". Paragraph 0214; 0217; 0222; 0223. . Retrieved 2016/12/26.
• 2、 Kivrakidou, Olga,Braese, Stefan,Huelshorst, Frank,Griebenow, Nils. "Solid-phase synthesis of 5-biphenyl-2-yl-1h-tetrazoles". . p. 1143 - 1146. Retrieved 2007/10/03.