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

HRID 1937362Notes

Reaction equation

HRID 1937362 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 SnC2-2H2O (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-2f7befe43d9841beadc11965c19e92ec
Source dataset
uspto-grants-2002_05
Patent number
US06395735B2

Reaction notes

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