Water → HCID 21584293, compound

HRID 583250Notes

Reaction equation

HRID 583250 reaction equation
[CH2:1]([CH:3]1[CH2:12][C:11]2[C:6](=[CH:7][C:8]([N+:13]([O-:15])=[O:14])=[CH:9][CH:10]=2)[CH:5]=[N:4]1)[CH3:2].[BH4-].[Na+].O>CO>[CH2:1]([CH:3]1[CH2:12][C:11]2[C:6](=[CH:7][C:8]([N+:13]([O-:15])=[O:14])=[CH:9][CH:10]=2)[CH2:5][NH:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 21584327HCID 21584327, compound

Product 1

HCID 21584293HCID 21584293, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-ethyl-7-nitro-3,4-dihydroisoquinoline (15.8 g, Example 2(d)) in methanol (100 ml) at 0° C. was added sodium borohydride (4 g). After foaming had stopped, the reaction was poured into water (750 ml) and then the aqueous phase was extracted with ethyl acetate (3×300 ml). Evaporation gave 3-ethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline as a tan oil (15.8 g).

Workup

  1. extractionthe aqueous phase was extracted with ethyl acetate (3×300 ml)
  2. customEvaporation

Sources & evidence

ORD record
ord-5619672b846c4057968b630c6baa3b2f
Source dataset
uspto-grants-1999_07
Patent number
US05929085

Reaction notes

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