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

HRID 264037ノート

反応式

HRID 264037 の反応式
[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]

参加物

8

反応物 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 7732P-AnisidineHCID 5003444Sodium cyanoborohydride2 回

生成物 1

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

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5a5afbadf6b44418a6a479723f702ab6
出典データセット
uspto-grants-1997_07
特許番号
US05646140

反応ノート

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