Lithium Carbonate → 2-[(4-tert-Butylphenyl)amino]-6-chloro-3-nitrobenzoic acid

HRID 1720874Notes

Reaction equation

HRID 1720874 reaction equation
Cl[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([Cl:14])[C:3]=1[C:4]([OH:6])=[O:5].[C:15]([C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1)([CH3:18])([CH3:17])[CH3:16].C(=O)([O-])[O-].[Li+].[Li+]>C(O)CC>[C:15]([C:19]1[CH:20]=[CH:21][C:22]([NH:23][C:2]2[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([Cl:14])[C:3]=2[C:4]([OH:6])=[O:5])=[CH:24][CH:25]=1)([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 11125Lithium CarbonateHCID 698614-Tert-ButylanilineHCID 3506232,6-Dichloro-3-nitrobenzoic acid

Product 1

HCID 103157662-[(4-tert-Butylphenyl)amino]-6-chloro-3-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A mixture of 2,6-dichloro-3-nitrobenzoic acid (4.72 g, 0.02 mol), 4-tertbutylaniline (4.47 g, 0.03 mol), lithium carbonate (1.48 g, 0.02 mol), and 1-propanol (10 mL) was refluxed with stirring for 20 h. The solvent was evaporated and to the residue, water (30 mL) and benzene (50 mL) were added. The mixture was made strongly basic with sodium hydroxide and stirred for 1h. Orange precipitate was collected by filtration and washed with benzene and ether. Dry precipitate was dissolved in water and acidified with diluted hydrochloric acid. Resulting precipitate was collected and crystallized from acetone-water to give 4.55 (65%) of the desired product, mp 201°-204° C. Anal. (C31H27N7O6) C, H, N.

Workup

  1. temperaturewas refluxed
  2. customThe solvent was evaporated and to the residue, water (30 mL) and benzene (50 mL)
  3. additionwere added
  4. stirringstirred for 1h
  5. filtrationOrange precipitate was collected by filtration
  6. washwashed with benzene and ether
  7. customDry precipitate
  8. dissolutionwas dissolved in water
  9. customResulting precipitate
  10. customwas collected
  11. customcrystallized from acetone-water

Sources & evidence

ORD record
ord-392833ffc9ff406cb5b449bd3e6cf8fa
Source dataset
uspto-grants-1996_04
Patent number
US05508289

Reaction notes

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