2,4-Dimethylbenzylamine → 6,8-Dimethylisoquinolin-3-amine

HRID 250140노트

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HRID 250140 반응식
C(O[CH:4](OCC)[C:5](=[NH:8])OC)C.[CH3:12][C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:14]=1[CH2:20][NH2:21]>CO>[CH3:19][C:17]1[CH:16]=[C:15]2[C:4](=[C:13]([CH3:12])[CH:18]=1)[CH:5]=[N:8][C:20]([NH2:21])=[CH:14]2

참가 물질

4

반응물 2

HCID 667612,4-DimethylbenzylamineHCID 17874536Methyl 2,2-diethoxyethanecarboximidate

생성물 1

HCID 574766096,8-Dimethylisoquinolin-3-amine수율 90%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
70 °C

실험 절차

To a solution of methyl 2,2-diethoxyacetimidate (1.5 g, 9.3 mmol) in methanol (4.9 mL) was added (2,4-dimethylphenyl)methanamine (1.2 g, 8.9 mmol) dropwise at ambient temperature. The reaction flask was then placed into a preheated oil-bath and stirred at 70° C. for 16 h, then cooled and the volatiles removed under reduced pressure. The crude material was added dropwise to sulfuric acid (19.7 mL) at ambient temperature and stirred for 72 h. The flask was then placed into an ice-water bath, diluted with water (50 mL), and slowly neutralized to pH=10 with sodium hydroxide (10 N). As the reaction mixture became basic, an orange precipitate formed. This precipitate was filtered, washed with water, and dried to afford 6,8-dimethylisoquinolin-3-amine (1.37 g, 7.95 mmol, 90%). 1H NMR (400 MHz, MeOD) δ ppm 8.82 (s, 1H), 7.17 (s, 1H), 6.90 (s, 1H), 6.72 (s, 1H), 2.61 (s, 3H), 2.37 (s, 3H). MS (LC/MS) R.T.=0.77; [M+H]+=173.15.

후처리

  1. customThe reaction flask was then placed into a preheated oil-bath
  2. temperaturecooled
  3. customthe volatiles removed under reduced pressure
  4. additionThe crude material was added dropwise to sulfuric acid (19.7 mL) at ambient temperature
  5. stirringstirred for 72 h
  6. customThe flask was then placed into an ice-water bath
  7. additiondiluted with water (50 mL)
  8. customan orange precipitate formed
  9. filtrationThis precipitate was filtered
  10. washwashed with water
  11. customdried

출처 및 근거

ORD 기록
ord-ef5c9351941e43ea823dd64cd92184db
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863291B2

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