Sodium Dithionite → HCID 22464174, compound

HRID 1274911Notes

Reaction equation

HRID 1274911 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([CH:16]3[CH2:21][C:20]4[C:22]([N+:28]([O-])=O)=[CH:23][CH:24]=[C:25]([O:26][CH3:27])[C:19]=4[O:18][CH2:17]3)=[O:15])=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>CN(C)C=O.O>[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([CH:16]3[CH2:21][C:20]4[C:22]([NH2:28])=[CH:23][CH:24]=[C:25]([O:26][CH3:27])[C:19]=4[O:18][CH2:17]3)=[O:15])=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 22464173HCID 22464173, compound

Product 1

HCID 22464174HCID 22464174, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of N-[4-(4-morpholinyl)phenyl]-8-methoxy-5-nitro-3,4-dihydro-2H-1-benzopyran-3-carboxamide (1.2 g, 2.9 mmol) in N,N-dimethylformamide (10 mL) was added a solution of sodium dithionite (2.1 g, 12 mmol) in water (5 mL). The mixture was stirred at 55° C. for 3 h and the solvent was removed in vacuo. The residue was purified by column chromatography on silica gel using ethyl acetate as the eluent affording 273 mg of the title compound (55% yield): EIMS (70 eV) m/z (relative intensity) 383 (100, M+).

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-8c759e3a51c8409daa52a395477eea7b
Source dataset
uspto-grants-2000_12
Patent number
US06159971

Reaction notes

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