Potassium hydroxide ethanol → 2-[2-Hydroxy-5-(pyrrolidine-1-carbonyl)-phenyl]-quinoline-6-carboxylic Acid

HRID 1788413Notes

Reaction equation

HRID 1788413 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[C:15](=O)[CH3:16].C[O:19][C:20](=[O:30])[C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[C:23]([CH:28]=O)[CH:22]=1.[OH-].[K+].C(O)C>C(O)C>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[C:15]1[CH:16]=[CH:28][C:23]2[C:24](=[CH:25][CH:26]=[C:21]([C:20]([OH:30])=[O:19])[CH:22]=2)[N:27]=1

Participants

5

Reactant 3

HCID 21946426Potassium hydroxide ethanolHCID 46911801Methyl 4-amino-3-formylbenzoateHCID 576031221-[2-Hydroxy-5-(pyrrolidine-1-carbonyl)-phenyl]-ethanone

Product 1

HCID 1360964502-[2-Hydroxy-5-(pyrrolidine-1-carbonyl)-phenyl]-quinoline-6-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 18 (410 mg, 1.75 mmol) and Compound 7 (315 mg, 1.75 mmol) were dissolved in 30 mL of ethanol, 2.45 mL of a 10% KOH/ethanol solution was added and the mixture was refluxed overnight under argon. The ethanol was evaporated, the residue dissolved in water, and acidified with 3 mL of 1M HCl. The formed gel was solidified by addition of 30 mL of ethyl acetate and 30 mL of a saturated NaCl solution. The solid was filtered, awashed with water, and dried. Yield 302 mg (48%) Compound 19.

Workup

  1. temperaturethe mixture was refluxed overnight under argon
  2. customThe ethanol was evaporated
  3. dissolutionthe residue dissolved in water
  4. additionThe formed gel was solidified by addition of 30 mL of ethyl acetate and 30 mL of a saturated NaCl solution
  5. filtrationThe solid was filtered
  6. customdried

Sources & evidence

ORD record
ord-a50cb176a218444796fa053ada1da08f
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

Loading…