Tetrahydrofuran → HCID 67205513, compound

HRID 1259870Notes

Reaction equation

HRID 1259870 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:6]=[C:5]2[C:18]([OH:20])=[O:19].[CH2:21]1C[O:24][CH2:23][CH2:22]1.C(Cl)(=O)CC>N1C=CC=CC=1>[C:12]1([C:7]2[CH:6]=[C:5]([C:18]([OH:20])=[O:19])[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([NH:1][C:23](=[O:24])[CH2:22][CH3:21])[CH:3]=3)[N:8]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 62324Propionyl chlorideHCID 13782592HCID 13782592, compound

Product 1

HCID 67205513HCID 67205513, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

6-amino-2-phenylquinoline-4-carboxylic acid (378 mg, 1.4 mmol) was suspended in pyridine (0.2 mL) and anhydrous THF (25 mL), and propionyl chloride (370 mg, 4 mmol) was added dropwise to the suspension with vigorous stirring. After reflux for 1.5 hours, the reaction solution was concentrated to approximately 10 mL. To the residue, ethyl acetate was added, and the deposited precipitate was collected by filtration and washed with water and ethyl ether. The crystal was recrystallized from glacial acetic acid to obtain the title compound (362 mg, 1.13 mmol) as a yellow powder.

Workup

  1. temperatureAfter reflux for 1.5 hours
  2. concentrationthe reaction solution was concentrated to approximately 10 mL
  3. additionTo the residue, ethyl acetate was added
  4. filtrationthe deposited precipitate was collected by filtration
  5. washwashed with water and ethyl ether
  6. customThe crystal was recrystallized from glacial acetic acid

Sources & evidence

ORD record
ord-672e2efc0e2e46899e71954a60c8b714
Source dataset
uspto-grants-2013_06
Patent number
US08466290B2

Reaction notes

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