Morpholine → 2-Methyl-6-morpholin-4-yl-3-nitro-pyridin-4-ylamine

HRID 457559Notes

Reaction equation

HRID 457559 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([NH2:12])[CH:3]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>C(O)C>[CH3:8][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([NH2:12])[CH:3]=[C:2]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[N:7]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 184399466-Chloro-2-methyl-3-nitropyridin-4-amine

Product 1

HCID 184399272-Methyl-6-morpholin-4-yl-3-nitro-pyridin-4-ylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

To a pressure vessel, a mixture of 6-chloro-2-methyl-3-nitro-pyridin-4-ylamine (0.75 g, 4.00 mmol) and morpholine (1.40 mL, 16.0 mmol) in absolute ethanol (16 mL) was stirred at 120° C. for 3 days. Absolute ethanol was evaporated in vacuo and the crude product was dissolved in a mixture of THF:EtOAc and this then subjected on top of a silica gel pad. Elution with EtOAc gave, after evaporation, the title compound as a yellow solid (0.89 g, 93%): IR (KBr, cm−1) 3460, 3330, 1627, 1597, 1553, 1233, 1113; 1H NMR (400 MHz, DMSO) δ 7.13 (s, 2H), 5.89 (s, 1H), 3.66–3.63 (m, 4H), 3.46–3.44 (m, 4H), 2.50 (s, 3H); LCMS (+ESI, M+H+) m/z 239; HPLC: 99% (220 nm).

Workup

  1. customAbsolute ethanol was evaporated in vacuo
  2. dissolutionthe crude product was dissolved in a mixture of THF
  3. washElution with EtOAc
  4. customgave
  5. customafter evaporation

Sources & evidence

ORD record
ord-31edc6be9f0a488eba38c946508e997c
Source dataset
uspto-grants-2007_03
Patent number
US07189716B2

Reaction notes

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