Methanol → HCID 21936644, compound

HRID 1241719Notes

Reaction equation

HRID 1241719 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][N:18]=3)[CH:13]=[C:12]([CH2:20][CH2:21][C:22](=[O:29])[C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)[C:11]2=[O:30])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[BH4-].[Na+].CO>ClCCl>[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][N:18]=3)[CH:13]=[C:12]([CH2:20][CH2:21][CH:22]([OH:29])[C:23]3[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=3)[C:11]2=[O:30])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 21936615HCID 21936615, compound

Product 1

HCID 21936644HCID 21936644, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(3-nitrophenyl)-3-[3-oxo-3-(pyridin-4-yl)propyl]-1,8-naphthyridin-2(1H)-one (1.07 g, 2.7 mmol; prepared in Example 17) in dichloromethane (50 ml) was added sodium borohydride, and the mixture was admixed dropwise with methanol (30 ml) gradually while the reaction was monitored by TLC. After completion of the reaction, the mixture was evaporated, admixed with water, and filtered to give a solid which was dried. Recrystallization from DMF yielded 1-(3-nitrophenyl)-3-[3-hydroxy-3-(pyridin-4-yl)propyl]-1,8-naphthyridin-2(1H)-one (770 mg, 71%; mp 235–236° C./DMF).

Workup

  1. customAfter completion of the reaction
  2. customthe mixture was evaporated
  3. filtrationfiltered
  4. customto give a solid which
  5. customwas dried
  6. customRecrystallization from DMF

Sources & evidence

ORD record
ord-4207e2d0b6054d2a9d9e97d1de1139d5
Source dataset
uspto-grants-2006_10
Patent number
US07115623B2

Reaction notes

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