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

HRID 2302077Notes

Reaction equation

HRID 2302077 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[Cl:25])[C:5]([NH:7][C@@H:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=2)[CH2:11][CH2:10][C@H:9]1[OH:21])=[O:6].[C:26](OC(=O)C)(=[O:28])[CH3:27]>C1COCC1.C(N(CC)CC)C.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[Cl:25])[C:5]([NH:7][C@@H:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=2)[CH2:11][CH2:10][C@H:9]1[O:21][C:26](=[O:28])[CH3:27])=[O:6]

Participants

6

Reactant 2

HCID 7918Acetic AnhydrideHCID 21338528(+)-trans-1-(3,4-Dichlorobenzamido)-2-hydroxy-7-nitrotetraline

Product 1

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

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 113 (1.9 g, 0.005 mol) in THF (200 mL), triethylamine (1.3 mL), and a catalystic amount of 4-dimethylaminopyridine was treated with acetic anhydride (0.9 mL). After stirring over night, the solvent was evaporated and the residue treated with H2O. After 2 h, the mixture was extracted with EtOAc. The extracts were washed with 1 N H2SO4, brine, aqueous NaHCO3 and brine, then the solvent was dried and evaporated to give a floculant white solid (1.94 g) that had the appropriate nmr for the desired material.

Workup

  1. customthe solvent was evaporated
  2. additionthe residue treated with H2O
  3. extractionthe mixture was extracted with EtOAc
  4. washThe extracts were washed with 1 N H2SO4, brine, aqueous NaHCO3 and brine
  5. customthe solvent was dried
  6. customevaporated

Sources & evidence

ORD record
ord-d3d30635dc854a368cc9987803012d96
Source dataset
uspto-grants-2002_08
Patent number
US06429317B1

Reaction notes

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