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

HRID 322613Notes

Reaction equation

HRID 322613 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 SnCl2H2O (4 g). After 4 h, additional SnCl2—2H2O (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. customThe solvent was then evaporated
  2. filtrationthe mixture filtered
  3. customThe organics were separated
  4. washwashed with brine
  5. customdried
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-6a8428648ed549b78ad17b4491c25e5e
Source dataset
uspto-grants-2001_04
Patent number
US06211364B1

Reaction notes

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