Tetrahydrofuran → 5-(1-Hydroxy-2-{[1-(4-methoxyphenyl)propan-2-yl]amino}ethyl)quinoline-2,8-diol--hydrogen chloride (1/1)

HRID 1380135Notes

Reaction equation

HRID 1380135 reaction equation
[ClH:1].C([O:9][C:10]1[CH:11]=[CH:12][C:13]([C@@H:21]([OH:35])[CH2:22][NH:23][C@H:24]([CH3:34])[CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)=[C:14]2[C:19]=1[NH:18][C:17](=[O:20])[CH:16]=[CH:15]2)C1C=CC=CC=1.O1CCCC1>[Pd].O>[ClH:1].[OH:9][C:10]1[CH:11]=[CH:12][C:13]([C@@H:21]([OH:35])[CH2:22][NH:23][C@H:24]([CH3:34])[CH2:25][C:26]2[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=2)=[C:14]2[C:19]=1[NH:18][C:17](=[O:20])[CH:16]=[CH:15]2

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 692886148-(Benzyloxy)-5-[(1R)-1-hydroxy-2-{[(2R)-1-(4-methoxyphenyl)propan-2-yl]amino}ethyl]quinolin-2(1H)-one--hydrogen chloride (1/1)

Product 1

HCID 639515-(1-Hydroxy-2-{[1-(4-methoxyphenyl)propan-2-yl]amino}ethyl)quinoline-2,8-diol--hydrogen chloride (1/1)Yield 83.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of 3.5 g of 8-benzyloxy-5-{(1R)-1-hydroxy-2-[N-((1R)-2-(p-methoxyphenyl)-1-methylethyl)amino]ethyl}carbostyril hydrochloride, 240 mg of 10% palladium-charcoal, 100 ml of tetrahydrofuran and 10 ml of water is shaken at room temperature at an atmospheric pressure under a hydrogen atmosphere for 2 hours. Insoluble materials are collected by filtration and washed with an aqueous 10% ethanol solution. The filtrate and washings are combined, and the combined solution is concentrated under reduced pressure to remove solvent. The residue is crystallized with a mixture of ethanol, water and isopropyl ether, and crystalline precipitates are collected by filtration. 2.38 g of 8-hydroxy-5-{(1R)-1-hydroxy-2-[N-((1R)-2-(p-methoxyphenyl)-1-methylethyl)amino]ethyl}carbostyril hydrochloride are obtained as colorless crystals. Yield: 83%

Workup

  1. filtrationInsoluble materials are collected by filtration
  2. washwashed with an aqueous 10% ethanol solution
  3. concentrationthe combined solution is concentrated under reduced pressure
  4. customto remove solvent
  5. customThe residue is crystallized with a mixture of ethanol, water and isopropyl ether
  6. customcrystalline precipitates
  7. filtrationare collected by filtration

Sources & evidence

ORD record
ord-237fa20073f847788e4253bcca8fcc06
Source dataset
uspto-grants-1986_04
Patent number
US04579854

Reaction notes

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