Hydrochloric Acid → HCID 81445331、化合物

HRID 878596ノート

反応式

HRID 878596 の反応式
N([O-])=O.[Na+].S(=O)(=O)(O)O.N[C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][C:20]=1[CH2:21][CH3:22])[C:14]([O:16][CH3:17])=[O:15].[ClH:23]>C(O)(=O)C.Cl[Cu]>[Cl:23][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][C:20]=1[CH2:21][CH3:22])[C:14]([O:16][CH3:17])=[O:15]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 13399999Methyl 3-amino-4-ethylbenzoateHCID 23668193Sodium Nitrite

生成物 1

HCID 81445331HCID 81445331、化合物収率 38%

試薬・触媒・溶媒 2

HCID 62652Cuprous chloride触媒HCID 176Acetic Acid溶媒

反応条件

温度
5 °C

実験手順

Charge NaNO2 (579 mg, 8.37 mmol) and concentrated sulfuric acid (6 mL) to a flask. As methyl 3-amino-4-ethylbenzoate (1.37 g, 7.62 mmol, PREPARATION 5) in acetic acid (18 mL) was added at 0° C., color of the mixture turned to yellow, and then stirred at 5° C. for 1.5 h. The solution above was added to a dark mixture of CuCl (1.65 g, 16.65 mmol) in concentrated HCl (18 mL) slowly at 0° C., stirred for 2 h, and poured into ice water, extracted with DCM, the organic phase was concentrated to give 582 mg of the title compound (38%). 1H NMR (400 MHz, CDCl3): δ 1.25 (3H, t, J=8.0 Hz), 2.80 (2H, q, J=7.6 Hz), 3.91 (3H, s), 7.30 (1H, d, J=7.6 Hz), 7.85 (1H, dd, J=1.2, 7.6 Hz), 8.01 (1H, d, J=1.6 Hz).

後処理

  1. stirringstirred for 2 h
  2. extractionextracted with DCM
  3. concentrationthe organic phase was concentrated

出典と根拠

ORDレコード
ord-6ef9257967664abb8792119ab8ec4f97
出典データセット
uspto-grants-2015_03
特許番号
US08987461B2

反応ノート

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