HCID 57524526, compound → 1H-Indole-1-acetic acid, 4-amino-α-(4-chlorophenyl)-, methyl ester

HRID 1427199Notes

Reaction equation

HRID 1427199 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:13]2[C:21]3[C:16](=[C:17]([N+:22]([O-])=O)[CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1>C(OCC)(=O)C.[Pt]>[NH2:22][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:16]=1[CH:15]=[CH:14][N:13]2[CH:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[C:9]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 1

HCID 57524526HCID 57524526, compound

Product 1

HCID 681754161H-Indole-1-acetic acid, 4-amino-α-(4-chlorophenyl)-, methyl ester

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1 (8.28 g, 24.0 mmol) in ethyl acetate (240 mL) was degassed, at which point platinum on carbon (1.41 g of a 10% wt/wt mixture, 0.721 mmol) was added, and the resulting suspension was stirred under a hydrogen atmosphere (balloon). After 3 h, the reaction mixture was filtered through a short column of CELITE® eluting with EtOAc. The combined organics were concentrated in vacuo to afford the title compound 2a. m/z (ES) 315 (MH)+.

Workup

  1. additionwas added
  2. filtrationthe reaction mixture was filtered through a short column of CELITE®
  3. washeluting with EtOAc
  4. concentrationThe combined organics were concentrated in vacuo

Sources & evidence

ORD record
ord-12bc841f734040a2bc433d11bc21b179
Source dataset
uspto-grants-2015_01
Patent number
US08933113B2

Reaction notes

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