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

HRID 325854

反応式

HRID 325854 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 3283Diethyl Ether溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0ad400d692c740b59c71f96517a2c060
出典データセット
uspto-grants-1984_04
特許番号
US04443447

関連ノート

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