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

HRID 502473Notes

Reaction equation

HRID 502473 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-29429c4d0c6b431f8e812bf8458737fd
Source dataset
uspto-grants-2010_08
Patent number
US07776107B2

Reaction notes

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