7-Methoxy-3,4-dihydro-2H-1-benzopyran-3-amine--hydrogen chloride (1/1) → HCID 22100485, compound

HRID 1457748Notes

Reaction equation

HRID 1457748 reaction equation
Cl.[NH2:2][CH:3]1[CH2:12][C:11]2[C:6](=[CH:7][C:8]([O:13][CH3:14])=[CH:9][CH:10]=2)[O:5][CH2:4]1.[CH3:15][O:16][C:17]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:18]=1[C:19](Cl)=[O:20]>N1C=CC=CC=1>[Cl:26][C:23]1[CH:24]=[CH:25][C:17]([O:16][CH3:15])=[C:18]([CH:22]=1)[C:19]([NH:2][CH:3]1[CH2:12][C:11]2[C:6](=[CH:7][C:8]([O:13][CH3:14])=[CH:9][CH:10]=2)[O:5][CH2:4]1)=[O:20]

Participants

4

Reactant 2

HCID 30416007-Methoxy-3,4-dihydro-2H-1-benzopyran-3-amine--hydrogen chloride (1/1)HCID 123841765-Chloro-2-methoxybenzoyl chloride

Product 1

HCID 22100485HCID 22100485, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

15.1 g (70 mmol) of 3-amino-7-methoxychroman hydrochloride (Eur. J. Med. Chem. 11 (1976), 251-256) were dissolved in 80 ml of pyridine, and 14.8 g of 2-methoxy-5-chlorobenzoyl chloride were added at 0° C. The mixture was stirred at room temperature for 1.5 hours and at 60° C. for 1 hour. The cooled reaction mixture was partitioned between water and methylene chloride. The aqueous phase was extracted three times with methylene chloride. The combined organic phases were washed with 2N hydrochloric acid, water and bicarbonate solution. After drying and evaporation of the organic phase, the residue was dissolved in a little toluene and the product was precipitated with excess diethyl ether. 3-(5-chloro-2-methoxybenzamido)-7-methoxychroman of melting point 92°-93° C. was obtained.

Workup

  1. customThe cooled reaction mixture
  2. customwas partitioned between water and methylene chloride
  3. extractionThe aqueous phase was extracted three times with methylene chloride
  4. washThe combined organic phases were washed with 2N hydrochloric acid, water and bicarbonate solution
  5. customAfter drying
  6. customevaporation of the organic phase
  7. dissolutionthe residue was dissolved in a little toluene
  8. customthe product was precipitated with excess diethyl ether

Sources & evidence

ORD record
ord-d8e777ce2dad42efa9b7462aa268c901
Source dataset
uspto-grants-1998_12
Patent number
US05849755

Reaction notes

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