Methyl 2-methylindolizine-3-carboxylate → Methyl 2-methyl-1-nitrosoindolizine-3-carboxylate

HRID 502473ノート

反応式

HRID 502473 の反応式
[N:1]([O-:3])=O.[Na+].[CH3:5][C:6]1[CH:7]=[C:8]2[N:13]([C:14]=1[C:15]([O:17][CH3:18])=[O:16])[CH:12]=[CH:11][CH:10]=[CH:9]2>O.C(O)(=O)C>[CH3:5][C:6]1[C:7]([N:1]=[O:3])=[C:8]2[N:13]([C:14]=1[C:15]([O:17][CH3:18])=[O:16])[CH:12]=[CH:11][CH:10]=[CH:9]2

参加物

5

反応物 2

HCID 13735249Methyl 2-methylindolizine-3-carboxylateHCID 23668193Sodium Nitrite

生成物 1

HCID 57872297Methyl 2-methyl-1-nitrosoindolizine-3-carboxylate収率 82.3%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒2 回

実験手順

A solution of sodium nitrite (2.2 g, 31.90 mmol) in water (10 mL) was added slowly at 0-5° C. to a stirred solution of methyl 2-methylindolizine-3-carboxylate 2 (3.9 g, 20.61 mmol) in glacial acetic acid (50 mL). After 30 min, the brown reaction mixture was poured into water. Green crystals were collected by filtration, washed with water and then dried under vacuum to give 3.7 g of expected compound; m.p.: 131-132° C. 1H NMR (CDCl3): 9.63 (d, J=7.0 Hz, 1H), 8.39 (d, J=8.5 Hz, 1H), 7.74-7.69 (m, 1H), 7.23-7.18 (m, 1H), 4.03 (s, 3H), 3.26 (s, 3H), 13C NMR (CDCl3): δ 162.5, 154.5, 141.7, 135.7, 127.9, 123.2, 118.4, 118.3, 114.5, 51.7, 11.1. Analysis calculated for C11H10N2O3: C, 60.55; H, 5.54; N, 12.84, found: C, 60.65; H, 5.60; N, 12.90.

後処理

  1. filtrationGreen crystals were collected by filtration
  2. washwashed with water
  3. customdried under vacuum

出典と根拠

ORDレコード
ord-29429c4d0c6b431f8e812bf8458737fd
出典データセット
uspto-grants-2010_08
特許番号
US07776107B2

反応ノート

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