Methanol → 2-(3-Cyano-4-phenylpyrrole-1-yl)-5-hydroxyisonicotinic acid ethyl ester

HRID 1516603Notes

Reaction equation

HRID 1516603 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[C:5]1[C:10]([O:11]CC2C=CC=CC=2)=[CH:9][N:8]=[C:7]([N:19]2[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:21]([C:30]#[N:31])=[CH:20]2)[CH:6]=1)[CH3:2].CO>[C].[Pd].C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:32])[C:5]1[C:10]([OH:11])=[CH:9][N:8]=[C:7]([N:19]2[CH:23]=[C:22]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:21]([C:30]#[N:31])=[CH:20]2)[CH:6]=1)[CH3:2]

Participants

5

Reactant 2

HCID 887MethanolHCID 594778055-Benzyloxy-2-(3-cyano-4-phenylpyrrole-1-yl)isonicotinic acid ethyl ester

Product 1

HCID 594778862-(3-Cyano-4-phenylpyrrole-1-yl)-5-hydroxyisonicotinic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-benzyloxy-2-(3-cyano-4-phenylpyrrole-1-yl)isonicotinic acid ethyl ester in a mixed solvent of methanol (2 mL) and ethyl acetate (2 mL) was added palladium-carbon powder (0.020 g), and this mixture was stirred at room temperature under a hydrogen atmosphere for 30 minutes. The insoluble material was removed by suction through a Celite pad. This filtrate was concentrated under reduced pressure. This obtained solid was washed with diethyl ether, dried to give the title compound (0.040 g).

Workup

  1. customThe insoluble material was removed by suction through a Celite pad
  2. concentrationThis filtrate was concentrated under reduced pressure
  3. washThis obtained solid was washed with diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-aaab336be6614b728a40df4471a6e34f
Source dataset
uspto-grants-2012_07
Patent number
US08227500B2

Reaction notes

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