Sodium Dithionite → N-(3-amino-4-methylphenyl)-3-(2-cyanopropan-2-yl)benzamide

HRID 1800725Notes

Reaction equation

HRID 1800725 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:22]=[CH:23][CH:24]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([N+:19]([O-])=O)[CH:13]=1)=[O:10])([CH3:5])[CH3:4])#[N:2].S(S([O-])=O)([O-])=O.[Na+].[Na+]>O1CCCC1>[NH2:19][C:14]1[CH:13]=[C:12]([NH:11][C:9](=[O:10])[C:8]2[CH:22]=[CH:23][CH:24]=[C:6]([C:3]([C:1]#[N:2])([CH3:5])[CH3:4])[CH:7]=2)[CH:17]=[CH:16][C:15]=1[CH3:18]

Participants

4

Reactant 2

HCID 24489Sodium DithioniteHCID 671255393-(1-Cyano-1-methylethyl)-N-(4-methyl-3-nitro-phenyl)benzamide

Product 1

HCID 67125542N-(3-amino-4-methylphenyl)-3-(2-cyanopropan-2-yl)benzamideYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of the above-mentioned crude product of 3-(1-cyano-1-methylethyl)-N-(4-methyl-3-nitrophenyl)benzamide in tetrahydrofuran (300 mL) was added an aqueous solution (500 mL) of sodium dithionite (78.1 g, 629 mmol), and the mixture was stirred at 100° C. for 2 hr. The organic layer of the reaction mixture was separated, and the aqueous layer was extracted with ethyl acetate (2×150 mL). The combined organic layer was washed with saturated brine (150 mL), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=98/2→0/100), and the fractions containing the object product were concentrated under reduced pressure to give the title compound (5.60 g, 38%) as a yellow solid.

Workup

  1. customThe organic layer of the reaction mixture was separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×150 mL)
  3. washThe combined organic layer was washed with saturated brine (150 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe insoluble material was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=98/2→0/100)
  8. additionthe fractions containing the object product
  9. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-0aeb23f84da44a5795c6a3fdd18d9e02
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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