Ammonium Chloride → 5-Hydroxy-5-phenyl-5,6,7,8-tetrahydroquinaldine

HRID 325854

Reaction equation

HRID 325854 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:9]=[C:10]1[CH2:19][CH2:18][CH2:17][C:16]2[N:15]=[C:14]([CH3:20])[CH:13]=[CH:12][C:11]1=2.N1C2C(=CC=CC=2)CCC1C.[Cl-].[NH4+]>C(OCC)C.Cl>[OH:9][C:10]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:19][CH2:18][CH2:17][C:16]2[N:15]=[C:14]([CH3:20])[CH:13]=[CH:12][C:11]1=2

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 962892-Methyl-1,2,3,4-tetrahydroquinolineHCID 103295782-methyl-7,8-dihydro-6H-quinolin-5-oneHCID 178418255HCID 178418255, compound

Product 1

HCID 133457525-Hydroxy-5-phenyl-5,6,7,8-tetrahydroquinaldine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of 0.155 moles of phenylmagnesium bromide in 250 ml of diethyl ether was added dropwise a solution of 2.0 g (0.124 mole) of 5-keto-5,6,7,8-tetrahydroquinaldine in 100 ml of diethyl ether. After all of the tetrahydroquinaldine had been added the mixture was then treated with an excess of a saturated aqueous ammonium chloride solution. The ether layer was separated, dried and evaporated to provide a residue. This residue was dissolved in dilute hydrochloric acid and the aqueous acid layer was then extracted sequentially with diethyl ether and hexane. The acid layer was then basified with aqueous sodium hydroxide. Filtration provided yellow solid 5-hydroxy-5-phenyl-5,6,7,8-tetrahydroquinaldine, which had a m.p. of 130°-134° C. after recrystallization from a dichloromethane-hexane mixture. Analysis: Calculated for C16H17NO: %C, 80.3; %H, 7.2; %N, 5.9; Found: %C, 80.2; %H, 7.2; %N, 5.5. The structural assignment was confirmed by infrared and nuclear magnetic resonance spectral analyses.

Workup

  1. customThe ether layer was separated
  2. customdried
  3. customevaporated
  4. customto provide a residue
  5. extractionthe aqueous acid layer was then extracted sequentially with diethyl ether and hexane
  6. filtrationFiltration

Sources & evidence

ORD record
ord-0ad400d692c740b59c71f96517a2c060
Source dataset
uspto-grants-1984_04
Patent number
US04443447

Linked notes

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