Acetic Acid → 4-methoxy-N-(propan-2-yl)aniline

HRID 264037노트

반응식

HRID 264037 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[C:10](O)(=O)[CH3:11].[C:14]([BH3-])#N.[Na+].Cl>CO.C1COCC1.CC(C)=O>[CH:10]([NH:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)([CH3:11])[CH3:14]

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 7732P-AnisidineHCID 5003444Sodium cyanoborohydride2회

생성물 1

HCID 27594984-methoxy-N-(propan-2-yl)aniline

시약·촉매·용매 3

HCID 180Acetone용매HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 4-methoxy-phenylamine (1.24 g) in methanol (15 mL) at ambient temperature was added successively, glacial acetic acid (415 mg), acetone (669 mg), and 1M sodium cyanoborohydride in THF (12.7 mL). The reaction mixture was stirred overnight at room temperature. The pH was adjusted to 2 with 6N HCl and stirred for 30 minutes after which time the excess sodium cyanoborohydride was completely quenched. The pH was then adjusted to 8.5 with 1N NaOH and the resultant solution extracted with diethyl ether (2×50 mL) and ethyl acetate (50 mL). The oganic extracts were combined, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (1.42 g) as a yellow oil. 1H NMR (300 MHz, CDCl3): d 1.18(d, J=6.1 Hz, 6H), 2.92(br s, 1H), 3.55(m, 1H), 3.75(s, 3H), 6.57(d, J=9.1 Hz, 2H), 6.78(d, J=8.8 Hz, 2H) TLC (EtOAc/Hex (2:3)): Rf =0.72.

후처리

  1. customwas completely quenched
  2. extractionthe resultant solution extracted with diethyl ether (2×50 mL) and ethyl acetate (50 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-5a5afbadf6b44418a6a479723f702ab6
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05646140

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