Ammonia → 7-nitro-1H-indole-2-carboxamide

HRID 1851364Notes

Reaction equation

HRID 1851364 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]([OH:15])=O)=[CH:9]2)([O-:3])=[O:2].[N:16]1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.N>O.CN(C)C=O>[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]([NH2:16])=[O:15])=[CH:9]2)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 814097-nitro-1H-indole-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 473196987-nitro-1H-indole-2-carboxamideYield 73.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 7-nitro-1H-indole-2-carboxylic acid (4.40 g), 1H-1,2,3-benzotriazol-1-ol (3.45 g) and N,N-dimethylformamide (80 mL) was added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (4.90 g) at room temperature, and the mixture was stirred for 20 min and 28% aqueous ammonia (7.8 mL) was added. The reaction mixture was stirred at room temperature for 1 hr, and water was added. The resulting crystals were filtrated, washed with water, and dried to give the title compound (3.21 g, yield 73%) as yellow crystals. melting point 297-298° C. (decomposition).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 hr
  2. filtrationThe resulting crystals were filtrated
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-4921a698a3064b3fae56966a37d6cdb4
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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