Potassium Carbonate → 2-(Methoxymethyl)-4-nitroaniline

HRID 411094Notes

Reaction equation

HRID 411094 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:5]=1OCC(N)=O.C(=O)([O-])[O-].[K+].[K+].C[N:25]1CCCC1=O>>[CH3:1][O:2][CH2:3][C:4]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:5]=1[NH2:25]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 11333911HCID 11333911, compound

Product 1

HCID 114011432-(Methoxymethyl)-4-nitroaniline

Conditions

Temperature
100 °C

Procedure

20 g of the 2-(2-methoxymethyl-4-nitrophenoxy)acetamide made in step 1 are dissolved in 55 ml of N-methylpyrrolidone, mixed with 29 g of potassium carbonate and heated for 3 hours at 100° C. Subsequently the reaction mixture is cooled to room temperature and the solvent is removed in vacuum at 60 to 80° C. The remaining residue is crystallized by addition of 100 ml water. 8.8 g of a yellowish product are obtained with a melting point of 90 to 92° C.

Workup

  1. temperatureSubsequently the reaction mixture is cooled to room temperature
  2. customthe solvent is removed in vacuum at 60 to 80° C
  3. customThe remaining residue is crystallized by addition of 100 ml water

Sources & evidence

ORD record
ord-0c92d5c414f548139dfaa08f55922cbf
Source dataset
uspto-grants-2003_05
Patent number
US06558433B2

Reaction notes

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