Water → 6-Nitro-o-anisidine

HRID 44473

Reaction equation

HRID 44473 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].[C:12]([O-])([O-])=O.[K+].[K+].CI.O>CN(C=O)C>[CH3:12][O:11][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[NH2:1]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 41154952-Amino-3-Nitrophenol

Product 1

HCID 854916-Nitro-o-anisidineYield 90.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-amino-3-nitrophenol (19.25 g) and K2CO3 (19 g) in DMF (100 mL) was added MeI (11 mL) at room temperature and the mixture was stirred over night and then poured into water. The resulting precipitate was collected by filtration and the solid was washed with water to afford the desired product (19 g, 90%). 1H NMR (300 MHz, CDCl3) δ ppm 3.92 (s, 1H), 6.43 (br s, 1H), 6.61 (dd, 1H, J=7.5, 9.0 Hz), 6.89 (dd, 1H, J=0.9, 7.5 Hz), 7.73 (dd, 1H, J=0.9, 9.0 Hz); LC-MS: m/e=169 [M+1]+

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washthe solid was washed with water

Sources & evidence

ORD record
ord-5902f394338943068ba0956c4d2c0bee
Source dataset
uspto-grants-2013_09
Patent number
US08541411B2

Linked notes

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