Ethanol → Ethyl 2-(3,5-dimethylmorpholino)acetohydrazide
Reaction equation
C(O[C:4](=[O:14])[CH2:5][N:6]1[CH:11]([CH3:12])[CH2:10][O:9][CH2:8][CH:7]1[CH3:13])C.O.[NH2:16][NH2:17].[CH2:18](O)[CH3:19]>>[CH2:18]([CH:5]([N:6]1[CH:7]([CH3:13])[CH2:8][O:9][CH2:10][CH:11]1[CH3:12])[C:4]([NH:16][NH2:17])=[O:14])[CH3:19]Participants
4
Conditions
- Temperature
- 80 °C
Procedure
Ethyl-2-(3,5-dimethylmorpholino)acetate (0.19 g, 0.944 mmol) was dissolved in ethanol (4 mL) and hydrazine hydrate (0.047 g, 0.944 mmol) was added dropwise. The reaction mixture was stirred at 80° C. for 20 h and the reaction mixture was concentrated under reduced pressure to give the crude product, which was used without further purification in the subsequent step. (Crude yield: 97%). 1H NMR (400 MHz, DMSO-d6) δ 8.95 (s, 2H), 8.84 (s, 1H), 3.60-3.63 (m, 2H), 3.25-3.29 (m, 2H), 3.14 (s, 2H), 3.05 (s, 2H), 0.86-0.88 (m, 6H): LCMS m/z 188.12 [M+H]+, tR 4.716 min
Workup
- concentrationthe reaction mixture was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-8b2a2d4103fb489bb4794570639d9a21
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09266843B2
Reaction notes
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