Water → 2-Morpholino-5-nitropyridine

HRID 2236151Notes

Reaction equation

HRID 2236151 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C(N(CC)CC)C.O>ClCCl>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 8471TriethylamineHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 968722-Morpholino-5-nitropyridineYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-chloro-5-nitro-pyridine (5 g, 31 mmol), morpholine (13 mL, 155 mmol), and triethylamine (10 mL) in dichloromethane (30 mL) was stirred at room temperature for 3 hr. After the reaction, the reaction mixture was mixed with water, and two layers were separated. The aqueous layer was extracted with CH2Cl2 two times. Organic layers were collected, combined, washed with brine, dried over sodium sulfate, filtered, and concentrated to give 4-(5-nitro-pyridin-2-yl)-morpholine (6.48 gm, 100%) as a yellow solid. LCMS calcd for C9H11N3O3 (m/e) 209, obsd 210 (M+H).

Workup

  1. customAfter the reaction
  2. customwere separated
  3. extractionThe aqueous layer was extracted with CH2Cl2 two times
  4. customOrganic layers were collected
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-13ea9fe10c494b2fb5bc65a10410a364
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

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