2-Benzyl-4-(3,4-dihydroxyphenyl)-7-hydroxy-8-nitro-1,2,3,4-tetrahydroisoquinoline hydrobromide → 8-Amino-4-(3,4-dihydroxyphenyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide

HRID 54674Notes

Reaction equation

HRID 54674 reaction equation
[BrH:1].C([N:9]1[CH2:18][CH:17]([C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([OH:26])[CH:20]=2)[C:16]2[C:11](=[C:12]([N+:28]([O-])=O)[C:13]([OH:27])=[CH:14][CH:15]=2)[CH2:10]1)C1C=CC=CC=1>C(O)C>[BrH:1].[NH2:28][C:12]1[C:13]([OH:27])=[CH:14][CH:15]=[C:16]2[C:11]=1[CH2:10][NH:9][CH2:18][CH:17]2[C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([OH:26])[CH:20]=1

Participants

3

Reactant 1

HCID 147195632-Benzyl-4-(3,4-dihydroxyphenyl)-7-hydroxy-8-nitro-1,2,3,4-tetrahydroisoquinoline hydrobromide

Product 1

HCID 147195648-Amino-4-(3,4-dihydroxyphenyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromideYield 112.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

700 mg of 2-benzyl-4-(3,4-dihydroxyphenyl)-7-hydroxy-8-nitro-1,2,3,4-tetrahydroisoquinoline hydrobromide was dissolved in 14 ml of ethanol, and by adding thereto 0.07 g of 10% paradium-carbon, hydrogenation reaction was performed at 40° C. The reaction was over, the reaction mixture was filtered, and concentrated. The residue obtained was changed to precipitates by treatment with chloroform, the precipitates were collected by filtration, and dried, affording 590 mg of 8-amino-4-(3,4-dihydroxyphenyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide.

Workup

  1. additionby adding
  2. customwas performed at 40° C
  3. filtrationwas filtered
  4. concentrationconcentrated
  5. customThe residue obtained
  6. customto precipitates by treatment with chloroform
  7. filtrationthe precipitates were collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-3b5fd5de2ada487991e47aefd847ab46
Source dataset
uspto-grants-1997_04
Patent number
US05623074

Reaction notes

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