Aminoammonium hydroxide → 7,8,9,10-Tetrahydropyridazino[4,5-a]indolizin-4(3H)-one

HRID 1021875Notes

Reaction equation

HRID 1021875 reaction equation
[CH:1]([C:3]1[C:4]([C:12]([O:14]C)=O)=[CH:5][N:6]2[C:11]=1[CH2:10][CH2:9][CH2:8][CH2:7]2)=O.[OH-].[NH3+:17][NH2:18]>>[CH:1]1[C:3]2=[C:11]3[N:6]([CH:5]=[C:4]2[C:12](=[O:14])[NH:18][N:17]=1)[CH2:7][CH2:8][CH2:9][CH2:10]3

Participants

3

Reactant 2

HCID 44558531Aminoammonium hydroxideHCID 86684350Methyl 1-formyl-5,6,7,8-tetrahydroindolizine-2-carboxylate

Product 1

HCID 866843517,8,9,10-Tetrahydropyridazino[4,5-a]indolizin-4(3H)-oneYield 83%

Conditions

Temperature
100 °C

Procedure

A 100 mL single-neck round-bottomed flask was charged with hydrazinium hydroxide (20 mL), methyl 1-formyl-5,6,7,8-tetrahydroindolizine-2-carboxylate 192a (2.5 g, 12.0 mmol). The reaction mixture was heated at 100° C. for 4 hours. After this time the reaction was cooled to room temperature and filtered to afford 192b as a yellow solid (1.9 g, 83%). MS: (M+H)+ 190.3. 1H NMR (500 MHz, DMSO) δ 11.44 (s, 1H), 8.03 (s, 1H), 7.42 (s, 1H), 4.18 (t, J=6.0 Hz, 2H), 2.96 (t, J=6.5 Hz, 2H), 1.98-1.93 (m, 2H), 1.87-1.82 (m, 2H).

Workup

  1. temperatureAfter this time the reaction was cooled to room temperature
  2. filtrationfiltered

Sources & evidence

ORD record
ord-cb09de9ed0f443829684b6d5a3f236b4
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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