(+)-trans-1-(3,4-Dichlorobenzamido)-2-acetoxy-7-nitrotetraline → (+)-trans-1-(3,4-Dichlorobenzamido)-2-acetoxy-7-aminotetraline

HRID 2302078Notes

Reaction equation

HRID 2302078 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[Cl:28])[C:5]([NH:7][C@@H:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([N+:18]([O-])=O)[CH:16]=2)[CH2:11][CH2:10][C@H:9]1[O:21][C:22](=[O:24])[CH3:23])=[O:6]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[Cl:28])[C:5]([NH:7][C@@H:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([NH2:18])[CH:16]=2)[CH2:11][CH2:10][C@H:9]1[O:21][C:22](=[O:24])[CH3:23])=[O:6]

Participants

3

Reactant 1

HCID 21338526(+)-trans-1-(3,4-Dichlorobenzamido)-2-acetoxy-7-nitrotetraline

Product 1

HCID 12042344(+)-trans-1-(3,4-Dichlorobenzamido)-2-acetoxy-7-aminotetralineYield 107.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 114 (1.9 g) in DMF (100 mL) was treated with SnCl2-2H2O (4 g). After 4 h, additional SnCl22H2O (1 g) was added three times over three days. The solvent was then evaporated, the residue suspended in H2O-EtOAc, the mixture neutralized with 5N NaOH, and the mixture filtered. The. organics were separated, washed with brine, dried, and the solvent evaporated to give a brown foam (1.9 g).

Workup

  1. additionadditional SnCl22H2O (1 g) was added three times over three days
  2. customThe solvent was then evaporated
  3. filtrationthe mixture filtered
  4. customorganics were separated
  5. washwashed with brine
  6. customdried
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-e02eb76ba2bd40e3bcba89907a5377cc
Source dataset
uspto-grants-2002_08
Patent number
US06429317B1

Reaction notes

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