Water → HCID 20395306, compound

HRID 261207Notes

Reaction equation

HRID 261207 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:18]=[CH:17][C:7]2[CH2:8][CH:9]3[CH:13]([C:14](=[O:15])[C:6]=2[CH:5]=1)[CH2:12][N:11]([CH3:16])[CH2:10]3.O>C(O)C>[Cl:3][C:4]1[CH:18]=[CH:17][C:7]2[CH2:8][CH:9]3[CH:13]([CH:14]([OH:15])[C:6]=2[CH:5]=1)[CH2:12][N:11]([CH3:16])[CH2:10]3

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 20395303HCID 20395303, compound

Product 1

HCID 20395306HCID 20395306, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1.6 g of sodium borohydride in 20 ml of ethanol are added at 0°-5° to a solution of 10 g of 6-chloro-3a,4,9,9a-tetrahydro-2-methylbenz[f]isoindolin-4-one in 100 ml of ethanol, stirred at room temperature for a further hour, water is added and the mixture evaporated. The residue is taken up in 10% tartaric acid, the aqueous phase extracted with ether, mixed with 2 N caustic soda solution and extracted with ethyl acetate. The ethyl acetate phase is dried over sodium sulphate and evaporated. The residue is crystallised from methylene chloride/pentane to yield 6-chloro-3a,4,9,9a-tetrahydro-2-methylbenz[f]isoindolin-4-ol. M.P. 178°-182°.

Workup

  1. customthe mixture evaporated
  2. extractionthe aqueous phase extracted with ether
  3. additionmixed with 2 N caustic soda solution
  4. extractionextracted with ethyl acetate
  5. dry with materialThe ethyl acetate phase is dried over sodium sulphate
  6. customevaporated
  7. customThe residue is crystallised from methylene chloride/pentane

Sources & evidence

ORD record
ord-63a5eb6f52f74122ba24834adedbee54
Source dataset
uspto-grants-1979_08
Patent number
US04164583

Reaction notes

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