Methanol → 5-[1-Cyclopropylcarbonyloxy-2-(3,4-dimethoxyphenethylamino)ethyl]-8-cyclopropylcarbonyloxycarbostyril hydrochloride

HRID 27785

Reaction equation

HRID 27785 reaction equation
[CH:1]1([C:4]([OH:6])=[O:5])[CH2:3][CH2:2]1.[CH:7]1([C:10]([Cl:12])=[O:11])[CH2:9][CH2:8]1.Cl.O[CH:15]([C:30]1[CH:39]=[CH:38][C:37]([OH:40])=[C:36]2[C:31]=1[CH:32]=[CH:33][C:34](=[O:41])[NH:35]2)[CH2:16][NH:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=1.CO>C(OCC)C>[ClH:12].[CH:1]1([C:4]([O:6][CH:15]([C:30]2[CH:39]=[CH:38][C:37]([O:40][C:10]([CH:7]3[CH2:9][CH2:8]3)=[O:11])=[C:36]3[C:31]=2[CH:32]=[CH:33][C:34](=[O:41])[NH:35]3)[CH2:16][NH:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)=[O:5])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 887MethanolHCID 15655Cyclopropanecarboxylic acidHCID 77637Cyclopropanecarbonyl chlorideHCID 233420515-[1-Hydroxy-2-(3,4-dimethoxyphenethylamino)ethyl]-8-hydroxycarbostyril hydrochloride

Product 1

HCID 233420475-[1-Cyclopropylcarbonyloxy-2-(3,4-dimethoxyphenethylamino)ethyl]-8-cyclopropylcarbonyloxycarbostyril hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2 ml of cyclopropanecarboxylic acid and 1 ml of cyclopropanecarboxylic acid chloride were added to 500 mg of 5-[1-hydroxy-2-(3,4-dimethoxyphenethylamino)ethyl]-8-hydroxycarbostyril hydrochloride, and the mixture was allowed to react for 1 hour at a temperature of 80° C. After completion of the reaction, 10 ml of methanol was added to the reaction mixture while cooling with ice-water followed by addition of diethyl ether to crystallize the product. The crystals thus obtained were separated by filtration, washed with diethyl ether and recrystallized from a mixture of ethanol and acetone to obtain 210 mg of 5-[1-cyclopropylcarbonyloxy-2-(3,4-dimethoxyphenethylamino)ethyl]-8-cyclopropylcarbonyloxycarbostyril hydrochloride having a melting point of 167°-168° C. (with decomposition).

Workup

  1. customto react for 1 hour at a temperature of 80° C
  2. additionwas added to the reaction mixture
  3. customto crystallize the product
  4. customThe crystals thus obtained
  5. customwere separated by filtration
  6. washwashed with diethyl ether
  7. customrecrystallized from a mixture of ethanol and acetone

Sources & evidence

ORD record
ord-8294f87b96c34758a9476c5d5ebb2992
Source dataset
uspto-grants-1980_09
Patent number
US04223137

Linked notes

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