Aminoammonium hydroxide → 6,7,8,9-Tetrahydropyridazino[4,5-b]indolizin-1(2H)-one

HRID 519391Notes

Reaction equation

HRID 519391 reaction equation
[CH:1]([C:3]1[N:11]2[C:6]([CH2:7][CH2:8][CH2:9][CH2:10]2)=[CH:5][C:4]=1[C:12]([O:14]C)=O)=O.[OH-].[NH3+:17][NH2:18]>>[C:12]1(=[O:14])[C:4]2[CH:5]=[C:6]3[N:11]([C:3]=2[CH:1]=[N:18][NH:17]1)[CH2:10][CH2:9][CH2:8][CH2:7]3

Participants

3

Reactant 2

HCID 44558531Aminoammonium hydroxideHCID 86683769Methyl 3-formyl-5,6,7,8-tetrahydroindolizine-2-carboxylate

Product 1

HCID 676394086,7,8,9-Tetrahydropyridazino[4,5-b]indolizin-1(2H)-oneYield 75%

Conditions

Temperature
100 °C

Procedure

A 100-mL single-neck round-bottomed flask equipped with a reflux condenser was charged with methyl 3-formyl-5,6,7,8-tetrahydroindolizine-2-carboxylate (127d) (600 mg, 2.9 mmol) and hydrazinium hydroxide (20 mL). 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 127e as a yellow solid (413 mg, 75%). MS-ESI: (M+H)+ 190.1. 1H NMR (500 MHz, DMSO-d6) δ 12.17 (s, 1H), 8.24 (s, 1H), 6.33 (s, 1H), 4.16 (t, J=6.0 Hz, 2H), 2.88 (t, J=6.5 Hz, 2H), 2.00-1.96 (m, 2H), 1.84-1.79 (m, 2H).

Workup

  1. customA 100-mL single-neck round-bottomed flask equipped with a reflux condenser
  2. temperatureAfter this time the reaction was cooled to room temperature
  3. filtrationfiltered

Sources & evidence

ORD record
ord-caa7a3d175bb451a96fc43c20c127d6f
Source dataset
uspto-grants-2015_08
Patent number
US09115152B2

Reaction notes

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