Ammonium Chloride → 2-Methyl-6-(morpholin-4-yl)pyridin-3-amine

HRID 594099Notes

Reaction equation

HRID 594099 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[CH:4][C:3]=1[N+:14]([O-])=O.[Cl-].[NH4+]>C(O)C.O.[Fe]>[CH3:1][C:2]1[C:3]([NH2:14])=[CH:4][CH:5]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:7]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 82089554-(6-Methyl-5-nitro-2-pyridinyl)morpholine

Product 1

HCID 672085622-Methyl-6-(morpholin-4-yl)pyridin-3-amineYield 39.5%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A suspension of 4-(6-methyl-5-nitro-2-pyridinyl)morpholine (500 mg, 2.240 mmol), iron powder (375 mg, 6.72 mmol) and ammonium chloride (60 mg, 1.120 mmol) in ethanol (15 mL) and water (5 mL) was heated at reflux for 2 hours. The reaction mixture was filtered through a pad of celite and the pad washed with further ethyl acetate. The combined filtrate and washings were separated between ethyl acetate and saturated sodium bicarbonate and the organic phase was washed with water then brine. The organics were then separated, dried over magnesium sulphate and evaporated in vacuo to give the title compound (171 mg) as a pale brown solid. LCMS (2 min, formic) Rt 0.30 min, m/z (ES+) 194 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. filtrationThe reaction mixture was filtered through a pad of celite
  4. washthe pad washed with further ethyl acetate
  5. customThe combined filtrate and washings were separated between ethyl acetate and saturated sodium bicarbonate
  6. washthe organic phase was washed with water
  7. customThe organics were then separated
  8. dry with materialdried over magnesium sulphate
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-4c361ffa77eb4defa3a017b1df098726
Source dataset
uspto-grants-2016_01
Patent number
US09242972B2

Reaction notes

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