Lithium Hydroxide → 7-[(4'-tert-Butyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acid

HRID 841784Notes

Reaction equation

HRID 841784 reaction equation
[OH-].[Li+].C([O:5][C:6]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[C:13]([NH:18][C:19]([C:21]1[C:22]([C:27]3[CH:32]=[CH:31][C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:29][CH:28]=3)=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:20])[CH:12]=2)=[O:7])C>C(O)C.O>[C:33]([C:30]1[CH:29]=[CH:28][C:27]([C:22]2[C:21]([C:19]([NH:18][C:13]3[CH:12]=[C:11]4[C:16]([CH:17]=[C:8]([C:6]([OH:7])=[O:5])[CH:9]=[N:10]4)=[CH:15][CH:14]=3)=[O:20])=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:32][CH:31]=1)([CH3:36])([CH3:34])[CH3:35]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 698914667-[(4'-Tert-butyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acid ethyl ester

Product 1

HCID 227368827-[(4'-tert-Butyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acidYield 80.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Lithium hydroxide (20.0 mg, 0.48 mmol) was added to a mixture of 7-[(4′-tert-butyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acid ethyl ester (99 mg, 0.22 mmol) in 6 ml ethanol and 3 ml water. The reaction mixture was heated under reflux for 1.5 hr, then cooled to room temperature. The ethanol was removed in vacuo and aqueous hydrochloric acid solution was added (0.46ml of 0.961M solution, 0.44 mmol) to the resulting aqueous solution. The precipitate that formed was filtered, washed with water and air dried to yield the title compound as a white solid (75.1 mg, 80.8% yield).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 1.5 hr
  3. customThe ethanol was removed in vacuo and aqueous hydrochloric acid solution
  4. additionwas added (0.46ml of 0.961M solution, 0.44 mmol) to the resulting aqueous solution
  5. customThe precipitate that formed
  6. filtrationwas filtered
  7. washwashed with water and air
  8. customdried

Sources & evidence

ORD record
ord-491e196c50494d47ae95fb02bd85ea62
Source dataset
uspto-grants-2002_04
Patent number
US06369075B1

Reaction notes

Loading…