Hydrochloric Acid → HCID 19972525, compound

HRID 1452273Notes

Reaction equation

HRID 1452273 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, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

467 ml of a 1.48N solution of sodium borohydride in anhydrous dimethyl formamide was added over a period of 30 minutes, under 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, supra) in 1 liter of anhydrous dimethylformamide. The reaction mixture was stirred for 2.5 hours at ambient temperature. 88 ml of 2N aqueous hydrochloric acid solution was added while maintaining the temperature at 0°-5° C. 102 ml of 12.7N aqueous sodium hydroxide solution was then added. The mixture was poured into 6 liters of water, stirred for 3 hours, and filtered on a Buchner funnel. The filter cake was washed with 4N sodium hydroxide solution and then with water. The resultant white solid was crystallized from methanol to give 50 g of the title compound, m.p. 145°-147° C.

Workup

  1. temperaturewhile maintaining the temperature at 0°-5° C
  2. stirringstirred for 3 hours
  3. filtrationfiltered on a Buchner funnel
  4. washThe filter cake was washed with 4N sodium hydroxide solution
  5. customThe resultant white solid was crystallized from methanol

Sources & evidence

ORD record
ord-83ef092fb6844a29af4a24648175eabc
Source dataset
uspto-grants-1997_02
Patent number
US05605896

Reaction notes

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