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

HRID 51921Notes

Reaction equation

HRID 51921 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 (0.46 ml of 0.961 M 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 (0.46 ml of 0.961 M 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-4bc325f0ef854f58b2783d190b280e3f
Source dataset
uspto-grants-2004_03
Patent number
US06713489B2

Reaction notes

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