Hydrochloric Acid → 1-(4-Nitrophenyl)ethanamine

HRID 1779101

反応式

HRID 1779101 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[CH3:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:19].[Na+].Cl>CO>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([NH2:19])[CH3:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 7487p-NitroacetophenoneHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 5919951-(4-Nitrophenyl)ethanamine

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A suspension of 4′-nitroacetophenone (5.00 g, 30.3 mmol) and ammonium acetate (28.4 g, 378 mmol) in MeOH (75 mL) was stirred at room temperature for 20 minutes. Sodium cyanoborohydride (1.38 g, 21.2 mmol) was added and the resulting mixture stirred for 48 hours. Aqueous HCl (6 M, 40 mL) was added and the mixture was filtered. The filtrate was washed with Et2O (3×40 mL) then the aqueous phase was basified to pH 10 using KOH. The basified aqueous layer was extracted with DCM (3×30 mL) and the combined organic phases were dried (MgSO4), filtered and evaporated in vacuo to give the title compound A129 as an amorphous orange solid (3.00 g, 60%); 1H NMR (300 MHz, CDCl3) δ 8.22 (d, J=8.6 Hz, 2H), 7.57 (d, J=8.6 Hz, 2H), 4.27-4.33 (m, 1H), 2.20 (brs, 2H), 1.45 (d, J=6.6 Hz, 3H).

後処理

  1. stirringthe resulting mixture stirred for 48 hours
  2. filtrationthe mixture was filtered
  3. washThe filtrate was washed with Et2O (3×40 mL)
  4. extractionThe basified aqueous layer was extracted with DCM (3×30 mL)
  5. dry with materialthe combined organic phases were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

出典と根拠

ORDレコード
ord-a5b6a50b389b41ba8c191b9f6b54493e
出典データセット
uspto-grants-2016_02
特許番号
US09266864B2

関連ノート

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