Potassium Hydroxide → 1-Methyl-5-nitro-3-phenyl-1H-indole-2-carboxylic acid

HRID 2118121Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:3]1[C:20]([O:22]CC)=[O:21].[OH-].[K+]>>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:3]1[C:20]([OH:22])=[O:21]

Participants

Reactant 2

HCID 14797Potassium Hydroxide

HCID 69231753ethyl 1-methyl-5-nitro-3-phenyl-1H-indole-2-carboxylate

Product 1

HCID 215435181-Methyl-5-nitro-3-phenyl-1H-indole-2-carboxylic acid

Procedure

1-Methyl-5-nitro-3-phenyl-1H-indole-2-carboxylic acid was prepared from ethyl 1-methyl-5-nitro-3-phenyl-1H-indole-2-carboxylate by KOH hydrolysis as a yellowish solid: 1H NMR (DMSO-d6) δ 4.08 (s, 3H, 7.48-7.55 (m, 5H, 7.86 (d, J=9.2 Hz, 1H), 8.21 (dd, J=9.2, 2.3 Hz, 1H, 8.30 (d, J=2.3 Hz, 1H; MS (ESI) m/z 295 [M-H]−; HRMS calcd for C16H13N2O4: 297.0873; found (ESI+): 297.0867; Anal. calcd for C16H12N2O4.0.15H2O: C, 63.32; H, 4.25; N, 9.23. Found: C, 63.34; H, 3.87; N, 9.12.

Sources & evidence

ORD record: ord-ee1d392bde86411baa709234f5e10e0e
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07442805B2

Reaction notes

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