Ammonium formate → HCID 178509462, compound

HRID 1916286Notes

Reaction equation

HRID 1916286 reaction equation
C(O[C:4]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15]#[N:16])=[CH:12][CH:13]=2)[NH:8][C:7]=1[NH2:17])=[O:5])C.[CH:18]([O-])=O.[NH4+:21]>C(N)=O>[OH:5][C:4]1[C:6]2[C:14]3[C:9](=[CH:10][C:11]([C:15]#[N:16])=[CH:12][CH:13]=3)[NH:8][C:7]=2[N:17]=[CH:18][N:21]=1

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 59447949HCID 59447949, compound

Product 1

HCID 178509462HCID 178509462, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 713FormamideSolvent

Procedure

A solution of 2-amino-6-cyano-1H-indole-3-carboxylic acid ethyl ester (750 mg, 3.3 mmol) and ammonium formate (193 mg, 3.3 mmol) in 4 mL formamide was heated to 175° C. overnight. The reaction mixture was allowed to cool to room temperature then poured onto water. The resulting precipitate was collected by filtration to give 297 mg of the title compound as a black solid. 1H NMR (DMSO) δ 12.7 (1H, s, br), 12.5 (1H, s, br), 8.23 (1H, d, J=4), 8.10 (1H, d, J=8.1), 7.93 (1H, s), 7.61 (1H, dd, J=8.1, 1.4); LC-MS (1) Rt 1.12 min; m/z (ES−) 209.

Workup

  1. additionthen poured onto water
  2. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-cacba37b22bb45dd84d9275b059f3de3
Source dataset
uspto-grants-2013_12
Patent number
US08618121B2

Reaction notes

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