3-Benzyl-8-methoxy-1,2,3,4-tetrahydro-chromeno[3,4-c]pyridin-5-one → 8-Methoxy-1,2,3,4-tetrahydro-chromeno[3,4-c]pyridin-5-one

HRID 962632Notes

Reaction equation

HRID 962632 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]2[C:14]3[CH:15]=[CH:16][C:17]([O:23][CH3:24])=[CH:18][C:19]=3[O:20][C:21](=[O:22])[C:10]=2[CH2:9]1)C1C=CC=CC=1>CO.O1CCCC1.[Pd]>[CH3:24][O:23][C:17]1[CH:16]=[CH:15][C:14]2[C:11]3[CH2:12][CH2:13][NH:8][CH2:9][C:10]=3[C:21](=[O:22])[O:20][C:19]=2[CH:18]=1

Participants

5

Reactant 1

HCID 98835873-Benzyl-8-methoxy-1,2,3,4-tetrahydro-chromeno[3,4-c]pyridin-5-one

Product 1

HCID 131369188-Methoxy-1,2,3,4-tetrahydro-chromeno[3,4-c]pyridin-5-oneYield 49%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-benzyl-8-methoxy-1,2,3,4-tetrahydro-chromeno[3,4-c]pyridin-5-one (8.2 g, 26 mmol) in 150 mL of methanol and 100 mL of tetrahydrofuran is hydrogenated at room temperature over a palladium on carbon catalyst (0.85 g) for 18 hours. The catalyst is filtered and the filtrate evaporated. Recrystallization of the residue from acetonitrile with a small amount of added water gives 2.9 g (49%) of product; mp 179°-181° C.

Workup

  1. filtrationThe catalyst is filtered
  2. customthe filtrate evaporated
  3. customRecrystallization of the residue from acetonitrile with a small amount of added water

Sources & evidence

ORD record
ord-103750842fdb4b3f96836dc4d4c5ba68
Source dataset
uspto-grants-1998_06
Patent number
US05760050

Reaction notes

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