Chloroform → HCID 19990533, compound

HRID 1650221Notes

Reaction equation

HRID 1650221 reaction equation
[CH2:1]([CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][C:17]3[CH:26]=[CH:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:18]=3)=[CH:10][CH:11]=2)[C:6]1=[O:27])[CH2:2][CH2:3][CH3:4].[BH4-].[Na+].C(Cl)(Cl)[Cl:31]>CO.CCOCC.C(OCC)(=O)C>[ClH:31].[CH2:1]([CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][C:17]3[CH:26]=[CH:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:18]=3)=[CH:10][CH:11]=2)[CH:6]1[OH:27])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 3

HCID 6212ChloroformHCID 4311764Sodium borohydrideHCID 10666188HCID 10666188, compound

Product 1

HCID 19990533HCID 19990533, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of 2-butyl-3,4-dihydro-7-(2-quinolylmethoxy)-1(2H)-naphthalenone (718 mg) in methanol (7 ml) in an ice bath was added dropwise a solution of sodium borohydride (114 mg) in methanol (7 ml). The mixture was stirred for half an hour at the same temperature and then diluted with chloroform (80 ml). The solution was washed with water (80 ml). The aqueous layer was extracted three times with chloroform. The combined organic layers were washed with water, dried and concentrated in vacuo to give an oily residue. The residue was dissolved in ether (200 ml) and thereto N-hydrogen chloride in ethyl acetate (1 ml) was added dropwise with stirring in an ice bath. The precipitates were collected by filtration and washed with ether to yield 2-butyl-7-(2-quinolylmethoxy)-1,2,3,4-tetrahydro-1-naphthol hydrochloride (700 mg). mp: 128°-131° C. IR (Nujol): 3220, 1607, 1598, 1501 cm-1. NMR (CD3OD, δ): 0.80-1.05 (3H, m), 1.10-2.17 (9H, m), 2.60-2.84 (2H, m), 4.30 (0.5H, d, J=7 Hz), 4.58 (0.5H, s), 5.70 (2H, s), 6.94-7.17 (2H, m), 7.25 (1H, d, J=2 Hz), 7.99 (1H, t, J=8 Hz), 8.18 (1H, d, J=8 Hz), 8.20 (1H, t, J=8 Hz), 8.32-8.43 (2H, m), 9.16 (1H, d, J=8 Hz).

Workup

  1. washThe solution was washed with water (80 ml)
  2. extractionThe aqueous layer was extracted three times with chloroform
  3. washThe combined organic layers were washed with water
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customto give an oily residue
  7. stirringwith stirring in an ice bath
  8. filtrationThe precipitates were collected by filtration
  9. washwashed with ether

Sources & evidence

ORD record
ord-7845f9cd1f8c440b853989b27287d080
Source dataset
uspto-grants-1990_05
Patent number
US04923881

Reaction notes

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