N-(7-(benzyloxy)-9H-carbazol-2-yl)-N-methylformamide → N-(7-hydroxy-9H-carbazol-2-yl)-N-methylformamide

HRID 1425571Notes

Reaction equation

HRID 1425571 reaction equation
C([O:8][C:9]1[CH:21]=[C:20]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]([N:22]([CH3:25])[CH:23]=[O:24])=[CH:17][C:18]=3[NH:19]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:21]=[C:20]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]([N:22]([CH3:25])[CH:23]=[O:24])=[CH:17][C:18]=3[NH:19]2)=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 86651370N-(7-(benzyloxy)-9H-carbazol-2-yl)-N-methylformamide

Product 1

HCID 58225218N-(7-hydroxy-9H-carbazol-2-yl)-N-methylformamideYield 94.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To N-(7-(benzyloxy)-9H-carbazol-2-yl)-N-methylformamide (110 mg, 0.33 mmol) in 50 mL MeOH was added Palladium on activated carbon (50 mg). The mixture was stirred at rt under H2 atmosphere for 15 h. Solid was filtered off and the filtrate was concentrated to afford N-(7-hydroxy-9H-carbazol-2-yl)-N-methylformamide as a brown solid (75 mg, 94%). This material was used directly for the next reaction without purification. MS (ESI) m/z 241 (M+H+).

Workup

  1. filtrationSolid was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9b26967abab34aa6a46463708bebf69a
Source dataset
uspto-grants-2015_01
Patent number
US08932557B2

Reaction notes

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