Sodium Dithionite → HCID 24962078, compound

HRID 1694648Notes

Reaction equation

HRID 1694648 reaction equation
[CH2:1]([O:4][C:5](=[O:34])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][O:13][C:14]2[CH:23]=[C:22]3[C:17]([C:18](=[O:33])[C:19]([C:24]4[CH:29]=[CH:28][C:27]([N+:30]([O-])=O)=[CH:26][CH:25]=4)=[CH:20][O:21]3)=[CH:16][CH:15]=2)[CH:7]=1)[CH:2]=[CH2:3].S(S([O-])=O)([O-])=O.[Na+].[Na+]>O1CCCC1.O>[NH2:30][C:27]1[CH:26]=[CH:25][C:24]([C:19]2[C:18](=[O:33])[C:17]3[C:22](=[CH:23][C:14]([O:13][CH2:12][C:8]4[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=4)[C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:34])=[CH:15][CH:16]=3)[O:21][CH:20]=2)=[CH:29][CH:28]=1

Participants

5

Reactant 2

HCID 24489Sodium Dithionite2×HCID 67279019HCID 67279019, compound

Product 1

HCID 24962078HCID 24962078, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
62.5 °C

Procedure

A suspension of 3-[3-(4-nitrophenyl)-4-oxo-4H-chromen-7-yloxymethyl]benzoic acid allyl ester (164.6 mg, 0.36 mmol), prepared as described in Example 5d, and sodium dithionite (188 mg, 1.08 mmol) in tetrahydrofuran (8 ml) and water (4 ml) was heated at 60-65° C. for 1 hour. Additional sodium dithionite (1.13 g, 6.48 mmol) was added in 5 portions over 2 hours. The reaction mixture was stirred at 60-65° C. overnight. 1H NMR of the reaction mixture showed that the product was obtained without starting material. The reaction mixture was mixed with silica gel (2 g), solvent removed under reduced pressure, and the mixture applied to a column. The silica gel mixture was purified by flash chromatography, eluting with methylene chloride/methanol (98/2) to give prop-2-enyl 3-{[3-(4-aminophenyl)-4-oxochromen-7-yloxy]methyl}benzoate as a yellow solid (99.6 mg, 65%); (ESI) m/z 428 (M+H)+.

Workup

  1. customprepared
  2. customwas obtained
  3. additionThe reaction mixture was mixed with silica gel (2 g), solvent
  4. customremoved under reduced pressure
  5. customThe silica gel mixture was purified by flash chromatography
  6. washeluting with methylene chloride/methanol (98/2)

Sources & evidence

ORD record
ord-9535a8d3aa5a4d8c9dbb61a8bdac85bc
Source dataset
uspto-grants-2012_04
Patent number
US08158810B2

Reaction notes

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