Toluene → Ethyl 9-bromo-5,6,7,8-tetrahydroacridine-3-carboxylate

HRID 520821노트

반응식

HRID 520821 반응식
O=[C:2]1[C:15]2[CH:14]=[CH:13][C:12]([C:16]([OH:18])=[O:17])=[CH:11][C:10]=2[NH:9][C:8]2[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=2.P(Br)(Br)([Br:21])=O.[C:24]1([CH3:30])C=CC=CC=1>>[Br:21][C:2]1[C:3]2[CH2:4][CH2:5][CH2:6][CH2:7][C:8]=2[N:9]=[C:10]2[C:15]=1[CH:14]=[CH:13][C:12]([C:16]([O:18][CH2:24][CH3:30])=[O:17])=[CH:11]2

참가 물질

4

반응물 3

HCID 1140TolueneHCID 24613Phosphorus oxybromideHCID 575164539-Oxo-5,6,7,8,9,10-hexahydro-acridine-3-carboxylic acid

생성물 1

HCID 67326061Ethyl 9-bromo-5,6,7,8-tetrahydroacridine-3-carboxylate

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온도
25 °C

실험 절차

A suspension of 9-oxo-5,6,7,8,9,10-hexahydro-acridine-3-carboxylic acid (1 g, 0.42 mmols) in toluene (10 mL) was heated with phosphorous oxybromide (3.54 g, 1.2 mmols) to 100° C. for 4 h. Reaction completion was monitored by TLC. Alter completion, the reaction mixture was cooled to 25° C., quenched with methanol (10 mL), concentrated the reaction mixture under vacuum and purified the crude product with silica gel column (60:120). Product eluted with 2% methanol in chloroform. Fractions were collected and concentrated to get the pure product as off white solid. This compound was taken as such to next step.

후처리

  1. customReaction completion
  2. customquenched with methanol (10 mL)
  3. concentrationconcentrated the reaction mixture under vacuum
  4. custompurified the crude product with silica gel column (60:120)
  5. washProduct eluted with 2% methanol in chloroform
  6. customFractions were collected
  7. concentrationconcentrated
  8. customto get the pure product as off white solid

출처 및 근거

ORD 기록
ord-5de1d80f3c454534a0a9023e2c5208f5
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09328093B2

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