Methyl 3-amino-5-morpholino-2-nitrobenzoate → Methyl 2,3-diamino-5-morpholinobenzoate

HRID 44521

反応式

HRID 44521 の反応式
[NH2:1][C:2]1[C:3]([N+:18]([O-])=O)=[C:4]([CH:9]=[C:10]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]>CO.[Pd]>[NH2:18][C:3]1[C:2]([NH2:1])=[CH:11][C:10]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

参加物

4

反応物 1

HCID 58278827Methyl 3-amino-5-morpholino-2-nitrobenzoate

生成物 1

HCID 58279190Methyl 2,3-diamino-5-morpholinobenzoate収率 80.1%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

A mixture of methyl 3-amino-5-morpholino-2-nitrobenzoate, prepared as described in Example 26, step c (19.2 g, 68.3 mmol) and Pd/C (1.9 g) in MeOH (500 mL) in an autoclave under an atmosphere of H2 (4 atm) were stirred at room temperature for 3 h, When TLC analysis indicated complete consumption of starting material, the mixture was filtered and the filtrate was concentrated in-vacuo to afford the desired product as a brown solid (13.9 g, 80.1%). 1H NMR (300 MHz, DMSO-d6): δ ppm 6.62 (d, 1H, J=2.4 Hz), 6.54 (d, 1H, J=2.4 Hz), 5.84 (s, 2H), 4.75 (s, 2H), 3.76 (s, 3H), 3.70 (t, 4H, J=4.8 Hz), 2.85 (t, 4H, 4.8 Hz). LC-MS: m/e=252.1 [M+1]+.

後処理

  1. customprepared
  2. customconsumption of starting material
  3. filtrationthe mixture was filtered
  4. concentrationthe filtrate was concentrated in-vacuo

出典と根拠

ORDレコード
ord-9851b73079404bf68f50e05d75e79684
出典データセット
uspto-grants-2013_09
特許番号
US08541411B2

関連ノート

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