Isobutyryl chloride → HCID 10070761, compound

HRID 1885177Notes

Reaction equation

HRID 1885177 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][C:18]=1[CH3:24])=[CH:13][CH:12]=[CH:11][C:10]=2[O:25][CH3:26])(=[O:5])[CH2:2][CH2:3][CH3:4].[C:27](Cl)(=[O:31])[CH:28]([CH3:30])[CH3:29]>N1C=CC=CC=1>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:27](=[O:31])[CH:28]([CH3:30])[CH3:29])=[CH:19][C:18]=1[CH3:24])=[CH:13][CH:12]=[CH:11][C:10]=2[O:25][CH3:26])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 62325Isobutyryl chlorideHCID 11725437HCID 11725437, compound

Product 1

HCID 10070761HCID 10070761, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Butyryl-4-(4-hydroxy-2-methylphenylamino)-8-methoxyquinoline (2.0 g, 5.7 mmol) was suspended in pyridine (25 ml), isobutyryl choride (5 ml) added, and the mixture stirred for 17 hours at room temperature; the solid rapidly dissolved to give a clear solution. The pyridine was evaporated, and the residue taken up in dichloromethane and washed with aqueous sodium bicarbonate and brine, dried and evaporated. Recrystallisation from isopropyl ether gave 3-butyryl-4-(4-isobutyryloxy-2-methylphenylamino)-8-methoxyquinoline (0.87 g, 36%), m.p. 123°-125°.

Workup

  1. dissolutionthe solid rapidly dissolved
  2. customto give a clear solution
  3. customThe pyridine was evaporated
  4. washwashed with aqueous sodium bicarbonate and brine
  5. customdried
  6. customevaporated
  7. customRecrystallisation from isopropyl ether

Sources & evidence

ORD record
ord-2f01d7e3b7054ce9b4e1b1d24b65a04a
Source dataset
uspto-grants-1992_09
Patent number
US05143920

Reaction notes

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