Hydrazinium chloride → 1-Amino-2,4-dimethyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid methyl ester

HRID 222790

반응식

HRID 222790 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 583074511-Amino-2,4-dimethyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid methyl ester

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
160 °C

실험 절차

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).

후처리

  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%)

출처 및 근거

ORD 기록
ord-3bd340761fa441a3afbe1e7e93423670
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207347B2

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