Sodium borohydride → HCID 67081682, compound

HRID 1666303Notes

Reaction equation

HRID 1666303 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[C:10]([C:20]2[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=2)(SC2C=CC=CC=2)[C:9]2[C:4](=[CH:5][C:6]([O:28][CH3:29])=[CH:7][CH:8]=2)[CH2:3]1.[BH4-].[Na+]>CO.O1CCCC1.O.O.O.O.O.O.[Ni](Cl)Cl>[CH3:1][N:2]1[C:11](=[O:12])[CH:10]([C:20]2[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=2)[C:9]2[C:4](=[CH:5][C:6]([O:28][CH3:29])=[CH:7][CH:8]=2)[CH2:3]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 67081920HCID 67081920, compound

Product 1

HCID 67081682HCID 67081682, compound

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of 2-methyl-4-(3,5-dichlorophenyl)-4-(phenylsulfanyl)-7-methoxy-1,4-dihydro-3(2H)-isoquinolone (1.0 g) and nickel chloride hexahydrate (3.8 g) in methanol-tetrahydrofuran (3:1, 50 ml) was cooled to 0° C. Sodium borohydride (0.66 g) was added in small portions during 30 minutes at a temperature not exceeding 5° C. The slurry was filtered and the filtrate concentrated to dryness. The residue was partitioned between dichloromethane (200 ml) and aqueous sodium hydroxide (2M, 200 ml). The organic phase was dried and concentrated to dryness leaving crude 2-methyl-4-(3,5-dichlorophenyl)-7-methoxy-1,4-dihydro-3(2H)-isoquino-linone (0.7 g). The crude product was purified by chromatography on silica gel using a mixture of dichloromethane and ethyl acetate (8:2) as eluent. Crystallization from methanol afforded the pure title compound, m.p. 163-165° C.

Workup

  1. customexceeding 5° C
  2. filtrationThe slurry was filtered
  3. concentrationthe filtrate concentrated to dryness
  4. customThe residue was partitioned between dichloromethane (200 ml) and aqueous sodium hydroxide (2M, 200 ml)
  5. customThe organic phase was dried
  6. concentrationconcentrated to dryness
  7. customleaving crude 2-methyl-4-(3,5-dichlorophenyl)-7-methoxy-1,4-dihydro-3(2H)-isoquino-linone (0.7 g)
  8. customThe crude product was purified by chromatography on silica gel using
  9. additiona mixture of dichloromethane and ethyl acetate (8:2) as eluent
  10. customCrystallization from methanol

Sources & evidence

ORD record
ord-e560d6cb13d9418989c0024eeef2d716
Source dataset
uspto-grants-2011_10
Patent number
US08044067B2

Reaction notes

Loading…