Stannous chloride dihydrate → N-(4-amino-2-methylphenyl)benzamide

HRID 562676Notes

Reaction equation

HRID 562676 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[NH:11][C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O.O.[Sn](Cl)Cl.C([O-])(O)=O.[Na+]>C(OCC)(=O)C>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([NH:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:2]([CH3:1])[CH:7]=1

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 2835288N-(2-methyl-4-nitrophenyl)benzamide

Product 1

HCID 3245571N-(4-amino-2-methylphenyl)benzamideYield 97.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of N-(2-methyl-4-nitrophenyl)benzamide (0.256 g, 1.0 mmol) and tin(II) chloride dihydrate (0.89 g, 3.96 mmol) in ethyl acetate (6 mL) was heated at 70° C. for 19 hr. The reaction mixture was then chilled, poured onto 50 mL ice, basified with 5% NaHCO3 (20 mL), extracted into EtOAc, washed with brine, dried and concentrated in vacuo to give N-(4-amino-2-methylphenyl)-benzamide (0.22 g, 97%). ES-MS (M+H)+=227, (M+Na)+=249.

Workup

  1. temperatureThe reaction mixture was then chilled
  2. extractionextracted into EtOAc
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fad3ad333e5743fea00ebe425e67a7c6
Source dataset
uspto-grants-2011_11
Patent number
US08067428B2

Reaction notes

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