Ethanol → HCID 21074241, compound

HRID 1373179Notes

Reaction equation

HRID 1373179 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:25]=[C:26]([O:28][CH:29]([CH3:31])[CH3:30])[CH:27]=1)[C:12]([NH:14][C:15]1[N:20]=[CH:19][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:17][CH:16]=1)=[O:13])C1C=CC=CC=1.C(O)C>C1COCC1.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([CH:25]=[C:26]([O:28][CH:29]([CH3:31])[CH3:30])[CH:27]=1)[C:12]([NH:14][C:15]1[N:20]=[CH:19][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:17][CH:16]=1)=[O:13]

Participants

5

Reactant 2

HCID 702EthanolHCID 21074239HCID 21074239, compound

Product 1

HCID 21074241HCID 21074241, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 6-[(3-benzyloxy-5-isopropoxybenzoyl)amino]-3-pyridinecarboxylate (1.92 g, 4.57 mM) was dissolved in THF (100 ml) and then ethanol (100 ml) and 10% palladium on carbon (250 mg) were added. The reaction was stirred at ambient temperature under an atmosphere of hydrogen (balloon) for 20 hours and was then filtered through diatomaceous earth. The filtrates were concentrated under reduced pressure to give methyl 6-[(3-hydroxy-5-isopropoxybenzoyl)amino]-3-pyridinecarboxylate as a colourless solid (1.42 g); H1 NMR δ (d6-DMSO) 1.24 (6H d) 3.85 (3H s) 4.62 (1H sept) 6.49 (1H s) 6.97 (1H s) 7.04 (1H s) 8.30 (2H s) 8.89 (1H s) 9.67 (1H s) 11.01 (1H s br); [M+H]-331; [M−H] 329.

Workup

  1. filtrationwas then filtered through diatomaceous earth
  2. concentrationThe filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-11d81bda807844058cfc138dd546b4b5
Source dataset
uspto-grants-2007_01
Patent number
US07160906B2

Reaction notes

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