Hydrazinium chloride → HCID 58307451, compound

HRID 222790

Reaction equation

HRID 222790 reaction equation
[CH3:1][C:2]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([CH3:13])O[C:4](=[O:5])[CH:3]=1.Cl.[NH2:15][NH2:16]>C(O)C>[CH3:12][O:11][C:9]([C:8]1[C:2]([CH3:1])=[CH:3][C:4](=[O:5])[N:15]([NH2:16])[C:7]=1[CH3:13])=[O:10]

Participants

4

Reactant 2

HCID 115031Hydrazinium chlorideHCID 1704852H-Pyran-5-carboxylic acid, 4,6-dimethyl-2-oxo-, methyl ester

Product 1

HCID 58307451HCID 58307451, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of methyl isodehydroacetate (24.0 g, 132 mmol) and hydrazine monohydrochloride (9.6 g, 140 mmol) in ethanol (30 mL) was heated under microwave irradiation at 160° C. for 2 hours. It was filtered and the obtained solution was evaporated. The oil was partitioned between sat. aq. Na2CO3 and ethyl acetate (3×250 mL). The combined organic solution was washed with brine, dried (Na2SO4) and evaporated. The title product was purified by flash chromatography (yield 2.8 g, 10%). LC-MS (m/z) 197.0 (MH+); tR=0.57 (method C). 1H NMR (600 MHz, CDCl3): 2.20 (s, 3H, Me), 2.52 (s, 3H, Me), 3.88 (s, 3H, OMe), 5.16 (s, 2H, NH2), 6.35 (s, 1H, C5-H).

Workup

  1. filtrationIt was filtered
  2. customthe obtained solution was evaporated
  3. customThe oil was partitioned between sat. aq. Na2CO3 and ethyl acetate (3×250 mL)
  4. washThe combined organic solution was washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe title product was purified by flash chromatography (yield 2.8 g, 10%)

Sources & evidence

ORD record
ord-3bd340761fa441a3afbe1e7e93423670
Source dataset
uspto-grants-2012_06
Patent number
US08207347B2

Linked notes

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