2-Iodobenzoic acid → HCID 19425996, compound

HRID 742373Notes

Reaction equation

HRID 742373 reaction equation
I[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[C:14]([N+:19]([O-:21])=[O:20])[CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>>[CH3:11][C:12]1[CH:18]=[CH:17][C:15]([NH:16][C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]([OH:6])=[O:5])=[C:14]([N+:19]([O-:21])=[O:20])[CH:13]=1

Participants

4

Reactant 3

HCID 69412-Iodobenzoic acidHCID 69784-Methyl-2-nitroanilineHCID 11430Potassium Carbonate

Product 1

HCID 19425996HCID 19425996, compound

Conditions

Temperature
200 °C

Procedure

2-iodobenzoic 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-9daa6fce392a4f3e904bf6e945135306
Source dataset
uspto-grants-1996_09
Patent number
US05554632

Reaction notes

Loading…