Benzoyl chloride → HCID 18646602, compound

HRID 2249126Notes

Reaction equation

HRID 2249126 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-a0e78503c5cb48869a682b4fd0fd543b
Source dataset
uspto-grants-1991_08
Patent number
US05041673

Reaction notes

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