Dimethylformamide → HCID 20037288, compound

HRID 1904553Notes

Reaction equation

HRID 1904553 reaction equation
CN(C)C=O.[CH3:6][C:7]1([CH3:18])[CH2:12][CH2:11][C:10]2[CH:13]=[CH:14][C:15]([OH:17])=[CH:16][C:9]=2[O:8]1.[H-].[Na+].Cl[C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][N:23]=1>O>[CH3:6][C:7]1([CH3:18])[CH2:12][CH2:11][C:10]2[CH:13]=[CH:14][C:15]([O:17][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][N:23]=3)=[CH:16][C:9]=2[O:8]1

Participants

6

Reactant 4

HCID 6228Dimethylformamide3×HCID 24758Sodium hydrideHCID 783082-Chloro-5-nitropyridineHCID 110412812,2-dimethyl-3,4-dihydro-2H-1-benzopyran-7-ol

Product 1

HCID 20037288HCID 20037288, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Five milliliters of an N,N-dimethylformamide solution of 1.5 g of 2,3-dihydro-2,2-dimethyl-7-hydroxy-4H-1-benzopyran synthesized by the method of Referential Example 19 was added dropwise to a mixture of 0.35 g of sodium hydride and 4 ml of N,N-dimethylformamide. The mixture was stirred at room temperature for 0.5 hour, and 6 ml of an N,N-dimethylformamide solution of 2-chloro-5-nitropyridine (1.3 g) was added to the resulting reddish orange solution, and the mixture was stirred at room temperature for 5 hours. The reaction mixture was poured into 100 ml of water, and extracted with 100 ml of ethyl acetate. The extract was dried over magnesium sulfate, and concentrated. The residue was purified by column chromatography to give 2.1 g (yield 84%) of the desired product as a yellow liquid.

Workup

  1. stirringthe mixture was stirred at room temperature for 5 hours
  2. extractionextracted with 100 ml of ethyl acetate
  3. dry with materialThe extract was dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-b1f8f6300d5543afbc0147096f6c4307
Source dataset
uspto-grants-1989_06
Patent number
US04838924

Reaction notes

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