HCID 117727660, compound → HCID 13917041, compound

HRID 517622Notes

Reaction equation

HRID 517622 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4](=O)[CH2:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([N+:14]([O-])=O)=[CH:8][C:7]=1[N+:17]([O-])=O>ClCCl.CO.[Pd]>[CH3:1][O:2][C:3]([C:4]1[NH:17][C:7]2[C:6]([CH:5]=1)=[CH:11][C:10]([O:12][CH3:13])=[C:9]([NH2:14])[CH:8]=2)=[O:21]

Participants

5

Reactant 1

HCID 117727660HCID 117727660, compound

Product 1

HCID 13917041HCID 13917041, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 3-(5-methoxy-2,4-dinitro-phenyl)-2-oxo-propionic acid methyl ester (about 100.0 g, 0.32 mol) in a mixture of dichloromethane and methanol (about 1.5 L), 10% Pd/C (about 30 g, 50% wet) is added at about 25° C. The reaction mixture is stirred under hydrogen atmosphere at a temperature of about 25° C. over a period of about 4 hours. The resulting reaction mixture is filtered through celite pad and concentrated under reduced pressure to yield the product [6-amino-5-methoxy-1H-indole-2-carboxylic acid methyl ester] as yellow color solid (about 59 g, 80%).

Workup

  1. additionis added at about 25° C
  2. customThe resulting reaction mixture
  3. filtrationis filtered through celite pad
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2ca1e058f78d448c922d755ff7bba3fa
Source dataset
uspto-grants-2015_08
Patent number
US09115128B2

Reaction notes

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