4-Methyl-2-nitroaniline → HCID 19425996, compound

HRID 742341Notes

Reaction equation

HRID 742341 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[C:12](=[O:15])([O-])[O-:13].[K+].[K+]>>[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:2]2[C:3](=[CH:4][CH:5]=[CH:7][CH:8]=2)[C:12]([OH:13])=[O:15])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

3

Reactant 2

HCID 69784-Methyl-2-nitroanilineHCID 11430Potassium Carbonate

Product 1

HCID 19425996HCID 19425996, compound

Conditions

Temperature
200 °C

Procedure

2-1odobenzoic acid (5 g, 20.16 mmol), 4-methyl-2-nitroaniline (6.12 g, 40.32 mmol), potassium carbonate (2.8 g, 20.3 mmol) and Cul (0.2 g) were thoroughly mixed and heated to 200° C. for 1 hour. After cooling the solid reaction mixture was partitioned between ethyl acetate and aqueous sodium hydroxide (1M). The product precipitated from the aqueous phase on acidification with hydrochloric acid (4M). Yield 3.69 g, mp 209°-213° C.

Workup

  1. temperatureAfter cooling
  2. customthe solid reaction mixture
  3. customwas partitioned between ethyl acetate and aqueous sodium hydroxide (1M)
  4. customThe product precipitated from the aqueous phase on acidification with hydrochloric acid (4M)

Sources & evidence

ORD record
ord-e0d19cb219b940b6936d1062c1314c25
Source dataset
uspto-grants-1996_09
Patent number
US05554630

Reaction notes

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