Dimethylformamide → HCID 57476023, compound

HRID 1851403Notes

Reaction equation

HRID 1851403 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2.[Cl:16]N1C(=O)CCC1=O.CN(C)C=O>O>[NH2:1][C:2]1[C:3]([Cl:16])=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 31398ChlorosuccinimideHCID 111381941H-Indole-2-carboxylic acid, 7-amino-, ethyl ester

Product 1

HCID 57476023HCID 57476023, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 7-amino-1H-indole-2-carboxylate (2.30 g), N-chlorosuccinimide (1.40 g) and N,N-dimethylformamide (10 mL) was stirred at room temperature overnight. To the reaction mixture was added water, and the resulting crystals were filtrated, washed with water and dried. The obtained crystals were subjected to silica gel column chromatography and the title compound (1.59 g, yield 63%) was obtained as pale-yellow crystals from a fraction eluted with ethyl acetate-hexane (2:3, volume ratio). melting point 217-218° C. (decomposition).

Workup

  1. filtrationthe resulting crystals were filtrated
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-6f1904cf21a14c158381805d829b408c
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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