Acetic Acid → HCID 178498372、化合物

HRID 44503

反応式

HRID 44503 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].C(Cl)Cl.[CH3:24][C:25](O)=O>[Fe]>[CH3:24][C:25]1[NH:18][C:3]2[C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:9][C:10]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[CH:11][C:2]=2[N:1]=1

参加物

5

反応物 3

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 58278827Methyl 3-amino-5-morpholino-2-nitrobenzoate

生成物 1

HCID 178498372HCID 178498372、化合物収率 77%

試薬・触媒・溶媒 1

HCID 23925Iron触媒

実験手順

To a solution of methyl 3-amino-5-(4-morpholinyl)-2-nitrobenzoate (22 g) stirring at reflux in HOAc (400 mL) was added iron powder in portions (13 g). After the addition, the mixture was stirred at reflux for 5 h. It was cooled to room temperature and the solvent was removed in-vacuo. The residue was neutralized with aqueous Na2CO3 solution (1 L). It was extracted with EtOAc (500 mL×3). The combined organic layers were then concentrated in-vacuo and the residue was purified by silica gel chromatography eluted with MeOH:DCM=1:30 to afford the desired product as a solid (16.6 g, yield 77%). 1H NMR (300 MHz, CDCl3): δ ppm 2.67 (s, 3H), 3.17 (t, 4H, J=4.8 Hz), 3.90 (t, 4H, J=4.8 Hz), 3.98 (s, 3H), 7.44 (d, 1H, J=1.8 Hz), 7.54 (d, 1H, J=1.8 Hz); LC-MS: m/e=276 [M+1]+.

後処理

  1. additionAfter the addition
  2. temperatureat reflux for 5 h
  3. customthe solvent was removed in-vacuo
  4. extractionIt was extracted with EtOAc (500 mL×3)
  5. concentrationThe combined organic layers were then concentrated in-vacuo
  6. customthe residue was purified by silica gel chromatography
  7. washeluted with MeOH

出典と根拠

ORDレコード
ord-11df0b4a0a5748c59323ac6bebb39bcd
出典データセット
uspto-grants-2013_09
特許番号
US08541411B2

関連ノート

読み込み中…