Hydrochloric Acid → HCID 19972525, compound

HRID 2400162Notes

Reaction equation

HRID 2400162 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[C:9](=[O:10])[C:8]2[CH:11]=[CH:12][CH:13]=[C:14]([C:15](Cl)=[O:16])[C:7]=2[O:6][C:5]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl.[OH-].[Na+]>CN(C)C=O.O>[OH:16][CH2:15][C:14]1[C:7]2[O:6][C:5]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[C:4]([CH3:3])[C:9](=[O:10])[C:8]=2[CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 13122092HCID 13122092, compound

Product 1

HCID 19972525HCID 19972525, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

467 ml of a 1.48N sodium borohydride solution in dimethylformamide was added over a period of 30 minutes, with stirring at ambient temperature, to a solution of 100 g of 3-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carbonyl chloride (prepared as described in Da Re, P. et al., J. Med. Pharm. Chem. 2: 263 (1960)) in 1 liter of anhydrous dimethylformamide and the reaction mixture was stirred for 2.5 hours at ambient temperature. Maintaining the reaction mixture temperature at 0°-5° C., 88 ml of 2N hydrochloric acid was added to the mixture followed by addition of 102 ml of a 12.7N sodium hydroxide solution. The resultant mixture was poured into 6 liters of water, stirred for 3 hours, and filtered by suction. The solid, sequentially washed with a 4N sodium hydroxide solution and water, was then crystallized from methanol. Yield: 50 g of the title compound, melting point 145°-147° C.

Workup

  1. temperatureMaintaining the reaction mixture temperature at 0°-5° C.
  2. stirringstirred for 3 hours
  3. filtrationfiltered by suction
  4. washThe solid, sequentially washed with a 4N sodium hydroxide solution and water
  5. customwas then crystallized from methanol

Sources & evidence

ORD record
ord-9397d5ddc4af4406829ad86022412dc0
Source dataset
uspto-grants-1995_09
Patent number
US05453518

Reaction notes

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