Benzoyl chloride → HCID 18646602, compound

HRID 1030659Notes

Reaction equation

HRID 1030659 reaction equation
[NH2:1][C@@H:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C@@H:4]([Cl:12])[C@H:3]1[OH:13].[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)(O)[O-].[Na+]>O.C1(C)C=CC=CC=1>[C:14]([NH:1][C@@H:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C@@H:4]([Cl:12])[C@H:3]1[OH:13])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 15078246HCID 15078246, compound

Product 1

HCID 18646602HCID 18646602, compoundYield 45.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

To a mixture of (±)-(1R,2S,3R)-3-amino-1-chloro-1,2,3,4-tetrahydro-2-naphthalenol (547 mg) in water (10 ml) and benzoylchloride (367 mg) in toluene (6 ml) was added dropwise a solution of sodium bicarbonate (420 mg) in water (10 ml) over a period of 30 minutes. Stirring was maintained at room temperature for an additional period of 30 minutes. The mixture was extracted with chloroform, washed with saturated aqueous sodium chloride and evaporated in vacuo. Recrystallization of the residue from a cyclohexane/ethyl acetate mixture yielded the title compound (357 mg) as a white solid.

Workup

  1. extractionThe mixture was extracted with chloroform
  2. washwashed with saturated aqueous sodium chloride
  3. customevaporated in vacuo
  4. customRecrystallization of the residue from a cyclohexane/ethyl acetate mixture

Sources & evidence

ORD record
ord-7e2c3a4cd77b446fb750e9fe8b58870c
Source dataset
uspto-grants-1992_04
Patent number
US05106861

Reaction notes

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