Sodium Hydroxide → 1-(2-Bromophenyl)-3,4-dihydroisoquinoline

HRID 1162972

반응식

HRID 1162972 반응식
[C:1]1([CH2:7][CH2:8][NH:9][C:10](=O)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Br:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.P(Cl)(Cl)(Cl)=O.[OH-].[Na+]>C1(C)C(C)=CC=CC=1>[Br:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:10]1[C:6]2[C:1](=[CH:2][CH:3]=[CH:4][CH:5]=2)[CH2:7][CH2:8][N:9]=1

참가 물질

6

반응물 4

HCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 24813Phosphorus oxychlorideHCID 6738402-bromo-N-(2-phenylethyl)benzamide

생성물 1

HCID 107795371-(2-Bromophenyl)-3,4-dihydroisoquinoline

시약·촉매·용매 1

HCID 7237O-Xylene용매

반응 조건

온도
100 °C

실험 절차

A suspension of 50.0 g (164 mmol) of N-phenylethyl-2-bromobenzamide and 27.9 g of phosphorus pentoxide in 200 ml of xylene was heated to 100° C. and admixed dropwise with 45.6 g (492 mmol) of phosphorus oxychloride. Subsequently, the reaction mixture was heated under reflux for 2 h. After cooling to 80° C., the reaction mixture was stirred into 4000 g of ice and adjusted to pH=12 with NaOH (solid). The organic phase was removed, the aqueous phase was extracted three times with 300 ml of toluene, and the combined organic phases were washed with 500 ml of water and subsequently dried over magnesium sulfate. After the desiccant had been filtered off and the solvent had been removed, the product was obtained as a yellow oil. The yield at a purity of approx. 99.0% was 46.9 g (164 mmol), 99.9% of theory.

후처리

  1. temperatureSubsequently, the reaction mixture was heated
  2. temperatureunder reflux for 2 h
  3. temperatureAfter cooling to 80° C.
  4. customThe organic phase was removed
  5. extractionthe aqueous phase was extracted three times with 300 ml of toluene
  6. washthe combined organic phases were washed with 500 ml of water
  7. dry with materialsubsequently dried over magnesium sulfate
  8. filtrationAfter the desiccant had been filtered off
  9. customthe solvent had been removed
  10. customthe product was obtained as a yellow oil
  11. customThe yield at a purity of approx. 99.0%

출처 및 근거

ORD 기록
ord-9b952819493b4769b5d1cf44d622c65b
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07820822B2

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