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

HRID 502473노트

반응식

HRID 502473 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

HCID 57872297Methyl 2-methyl-1-nitrosoindolizine-3-carboxylate수율 82.3%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매2회

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-29429c4d0c6b431f8e812bf8458737fd
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776107B2

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