Acetone → HCID 21425544, compound

HRID 259017Notes

Reaction equation

HRID 259017 reaction equation
[ClH:1].[NH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:9]=2[N+:13]([O-:15])=[O:14])[CH:4]1[OH:24].CO.C([BH3-])#N.[Li+].[CH3:31][C:32]([CH3:34])=O>O>[ClH:1].[CH2:17]([O:16][C:8]1[C:9]([N+:13]([O-:15])=[O:14])=[C:10]2[C:5](=[CH:6][CH:7]=1)[CH:4]([OH:24])[CH:3]([NH:2][CH:32]([CH3:34])[CH3:31])[CH2:12][CH2:11]2)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 887MethanolHCID 21425510HCID 21425510, compoundHCID 13171016319536-84-6

Product 1

HCID 21425544HCID 21425544, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 5.0 g. of 2-amino-6-benzyloxy-1-hydroxy-5-nitro-1,2,3,4-tetrahydronaphthalene hydrochloride in 50 ml. of methanol are added 5.0 g. of lithium cyanoborohydride and 150 ml. of acetone, and the mixture is stirred at room temperature for 3 hours. The reaction mixture is added in water and the resulting crystals are recovered by filtration, rinsed with water, dried and dissolved in alcoholic hydrochloric acid. After treatment with activated carbon, ethyl ether is added, whereupon 4.7 g. of 6-benzyloxy-2-isopropylamino-5-nitro-1-hydroxy-1,2,3,4-tetrahydronaphthalene hydrochloride is obtained as colorless needles melting at 268°-270° C.

Workup

  1. filtrationthe resulting crystals are recovered by filtration
  2. washrinsed with water
  3. customdried
  4. dissolutiondissolved in alcoholic hydrochloric acid
  5. additionAfter treatment with activated carbon, ethyl ether is added, whereupon 4.7 g

Sources & evidence

ORD record
ord-31efd4976c4f4a7ea54864a1a9c90ba0
Source dataset
uspto-grants-1977_07
Patent number
US04035512

Reaction notes

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