Methylamine → FG-7142

HRID 1085453Notes

Reaction equation

HRID 1085453 reaction equation
CO[C:3]([C:5]1[N:6]=[CH:7][C:8]2[NH:9][C:10]3[C:15]([C:16]=2[CH:17]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:4].[CH3:18][NH2:19]>CO>[CH3:18][NH:19][C:3]([C:5]1[N:6]=[CH:7][C:8]2[NH:9][C:10]3[C:15]([C:16]=2[CH:17]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:4]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 107704Methyl 9H-pyrido(3,4-b)indole-3-carboxylate

Product 1

HCID 4375FG-7142Yield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

12 g of β-carbolin-3-carboxylic acid methyl ester is suspended in 130 ml of methanol; 130 ml of 40% aqueous methylamine is added thereto and the whole is boiled at reflux for 2 hours. After cooling, the mixture is suction-filtered. By extraction with 300 ml of hot methanol and crystallization from dimethylformamide/hexane, the β-carbolin-3-carboxylic acid N-methylamide of melting point 264°-266° C. is isolated from the filter residue in 43% yield.

Workup

  1. temperatureat reflux for 2 hours
  2. temperatureAfter cooling
  3. filtrationthe mixture is suction-filtered
  4. extractionBy extraction
  5. customwith 300 ml of hot methanol and crystallization from dimethylformamide/hexane

Sources & evidence

ORD record
ord-1aa19bd488e4488f8303d7fac6287245
Source dataset
uspto-grants-1991_04
Patent number
US05010077

Reaction notes

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