Sodium borohydride → HCID 67081706, compound

HRID 1666310Notes

Reaction equation

HRID 1666310 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[C:10]([C:20]2[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[C:22]([O:28][CH3:29])[CH:21]=2)(SC2C=CC=CC=2)[C:9]2[C:4](=[CH:5][C:6]([O:30][CH3:31])=[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]([O:26][CH3:27])[CH:23]=[C:22]([O:28][CH3:29])[CH:21]=2)[C:9]2[C:4](=[CH:5][C:6]([O:30][CH3:31])=[CH:7][CH:8]=2)[CH2:3]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 67081860HCID 67081860, compound

Product 1

HCID 67081706HCID 67081706, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of 2-methyl-4-(3,5-dimethoxyphenyl)-4-(phenylsulfanyl)-7-methoxy-1,4-dihydro-3(2H)-isoquinolone (2.4 g) and nickel chloride hexahydrate (8.8 g) in methanol-tetrahydro-furan (3:1, 100 ml) was cooled to 0° C. Sodium borohydride (4.2 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-dimethoxyphenyl)-7-methoxy-1,4-dihydro-3(2H)-isoquinolinone (1.3 g). Crystallization from methanol afforded the pure compound, m.p. 137-139

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

Sources & evidence

ORD record
ord-c84cf7c4af9d4c568e4a4dacdc0634ce
Source dataset
uspto-grants-2011_10
Patent number
US08044067B2

Reaction notes

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