Pyridine → 2,8-Bis(isobutyryloxy)-5-(alpha-isopropylaminobutyryl)quinoline hydrochloride

HRID 27776Notes

Reaction equation

HRID 27776 reaction equation
N1[CH:6]=[CH:5][CH:4]=CC=1.[OH:7][C:8]1[CH:9]=[CH:10][C:11]([C:19](=[O:27])[CH:20]([NH:23][CH:24]([CH3:26])[CH3:25])[CH2:21][CH3:22])=[C:12]2[C:17]=1[NH:16][C:15](=[O:18])[CH:14]=[CH:13]2.[C:28]([Cl:33])(=[O:32])[CH:29]([CH3:31])[CH3:30].[CH2:34]([O:36]CC)C>O>[ClH:33].[C:28]([O:18][C:15]1[CH:14]=[CH:13][C:12]2[C:17](=[C:8]([O:7][C:34](=[O:36])[CH:5]([CH3:4])[CH3:6])[CH:9]=[CH:10][C:11]=2[C:19](=[O:27])[CH:20]([NH:23][CH:24]([CH3:26])[CH3:25])[CH2:21][CH3:22])[N:16]=1)(=[O:32])[CH:29]([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 62325Isobutyryl chlorideHCID 123741458-Hydroxy-5-[2-[(1-methylethyl)amino]-1-oxobutyl]-2(1H)-quinolinone

Product 1

HCID 233420772,8-Bis(isobutyryloxy)-5-(alpha-isopropylaminobutyryl)quinoline hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

20 ml of pyridine was added to 1 g of 8-hydroxy-5-(α-isopropylaminobutyryl)carbostyril, and 2 ml of isobutyryl chloride was added dropwise to the mixture while cooling with ice-water and stirring followed by stirring for 3 hours and for 2 hours at a temperature of 35°-40° C. After addition of about 200 ml of diethyl ether, the precipitate formed was stirred in a small amount of cold water and then washed successively with acetone and diethyl ehter. The resulting crystalline product was then recrystallized from acetone to obtain 0.6 g of 2,8-bis(isobutyryloxy)-5-(α-isopropylaminobutyryl)quinoline hydrochloride having a melting point of 214°-215° C. (with coloration and decomposition).

Workup

  1. additionwas added dropwise to the mixture
  2. stirringby stirring for 3 hours and for 2 hours at a temperature of 35°-40° C
  3. customthe precipitate formed
  4. washwashed successively with acetone and diethyl ehter
  5. customThe resulting crystalline product was then recrystallized from acetone

Sources & evidence

ORD record
ord-122cb8a1f5bd4c5bada97a3ab54252d8
Source dataset
uspto-grants-1980_09
Patent number
US04223137

Reaction notes

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