Pyridine → 8-isobutyryloxy-5-(alpha-Isopropylaminobutyryl)carbostyril hydrochloride

HRID 27775Notes

Reaction equation

HRID 27775 reaction equation
N1C=CC=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]>C(OCC)C>[ClH:33].[C:28]([O: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)(=[O:32])[CH:29]([CH3:31])[CH3:30]

Participants

5

Reactant 3

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

Product 1

HCID 233421038-isobutyryloxy-5-(alpha-Isopropylaminobutyryl)carbostyril hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

50 ml of pyridine was added to 2.5 g of 8-hydroxy-5-(α-isopropylaminobutyryl)carbostyril, and 5 ml of isobutyryl chloride was added dropwise to the mixture while cooling with ice-water and stirring followed by stirring for 2 hours. After addition of about 500 ml of diethyl ether, the precipitate formed was washed with diethyl ether and stirred in a small amount of cold water. The precipitate was separated by filtration, washed successively with a small amount of water, acetone and diethyl ether to obtain a crystalline product which was then recrystallized from acetone to obtain 2.1 g of 8-isobutyryloxy-5-(α-Isopropylaminobutyryl)carbostyril hydrochloride having a melting point of 231°-233° C. (with decomposition).

Workup

  1. additionwas added dropwise to the mixture
  2. stirringby stirring for 2 hours
  3. customthe precipitate formed
  4. washwas washed with diethyl ether
  5. stirringstirred in a small amount of cold water
  6. customThe precipitate was separated by filtration
  7. washwashed successively with a small amount of water, acetone and diethyl ether
  8. customto obtain a crystalline product which
  9. customwas then recrystallized from acetone

Sources & evidence

ORD record
ord-56865a89a47345e59c26c3b9497d1994
Source dataset
uspto-grants-1980_09
Patent number
US04223137

Reaction notes

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