4-Methyl-3-nitroaniline → HCID 178428208, compound

HRID 268274

Reaction equation

HRID 268274 reaction equation
[ClH:1].N([C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]3[N:21]=[CH:20][NH:19][C:17]3=2)[N:12]=[C:11]([CH3:22])[CH:10]=1)C1C=CC=CC=1.[CH3:23][C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][C:25]=1[N+:31]([O-:33])=[O:32]>C(O)C>[ClH:1].[CH3:23][C:24]1[CH:30]=[CH:29][C:27]([NH:28][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]4[N:21]=[CH:20][NH:19][C:17]4=3)[N:12]=[C:11]([CH3:22])[CH:10]=2)=[CH:26][C:25]=1[N+:31]([O-:33])=[O:32]

Participants

4

Reactant 2

HCID 83904-Methyl-3-nitroanilineHCID 178428198HCID 178428198, compound

Product 1

HCID 178428208HCID 178428208, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 10.85 g. (0.05 m.) of the compound of Example I, C., 7.6 g. (0.05 m.) of 4-methyl-3-nitroaniline and 500 ml. of ethanol was refluxed overnight. The reaction mixture was concentrated in vacuo to give 38 g. of crude product. It was then dissolved in 6000 ml. of MeOH and filtered hot. The MeOH filtrate was concentrated in vacuo to yield 27 g., m.p. 344°-345°C.

Workup

  1. additionA mixture of 10.85 g
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto give 38 g
  4. dissolutionIt was then dissolved in 6000 ml
  5. filtrationof MeOH and filtered hot
  6. concentrationThe MeOH filtrate was concentrated in vacuo
  7. customto yield 27 g

Sources & evidence

ORD record
ord-5a650ce85fff40e790f052503055eb84
Source dataset
uspto-grants-1976_03
Patent number
US03947434

Linked notes

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