Benzoyl chloride → trans-3-Benzamido-1,2,3,4-tetrahydro-2-naphthalenol

HRID 616983Notes

Reaction equation

HRID 616983 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][C@H:4]1[OH:13].[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O.C1C=CC=CC=1>[C:14]([NH:2][C@@H:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][C@H:4]1[OH:13])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 12878372rac-(2R,3R)-3-amino-1,2,3,4-tetrahydronaphthalen-2-ol hydrochloride

Product 1

HCID 12878375trans-3-Benzamido-1,2,3,4-tetrahydro-2-naphthalenol

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

To a well stirred solution of 3.62 g of trans-3-amino-1,2,3,4-tetrahydro-2-naphthalenol, hydrochloride (1:1) in 30 ml of water at 0-5° C is added 2.1 ml of benzoyl chloride in 10 ml of benzene. To this stirred two-phase mixture is added, over 30 minutes at 0°-5° C, a solution of 1.45 g of sodium hydroxide in 30 ml of water--precipitation of a pink solid begins immediately. After stirring the mixture for an additional 2 hours at 0°-5° C, the solid is filtered, washed with ether, and dried in vacuo to give 4.2 g of crude trans-3-benzamido-1,2,3,4-tetrahydro-2-naphthalenol.

Workup

  1. additionTo this stirred two-phase mixture is added, over 30 minutes at 0°-5° C
  2. customa solution of 1.45 g of sodium hydroxide in 30 ml of water--precipitation of a pink solid
  3. filtrationthe solid is filtered
  4. washwashed with ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-1d8d5486ccb94bb6a6472a274ac852e6
Source dataset
uspto-grants-1978_02
Patent number
US04076843

Reaction notes

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