Ammonium Chloride → 2-Methyl-6-[1-(phenylmethyl)-3-pyrrolidinyl]-3-pyridinamine

HRID 594111Notes

Reaction equation

HRID 594111 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4]([CH:11]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12]2)[N:3]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[CH3:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([CH:11]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12]2)[N:3]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 898759582-Methyl-3-nitro-6-[1-(phenylmethyl)-3-pyrrolidinyl]pyridine

Product 1

HCID 898759382-Methyl-6-[1-(phenylmethyl)-3-pyrrolidinyl]-3-pyridinamineYield 85%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-methyl-3-nitro-6-[1-(phenylmethyl)-3-pyrrolidinyl]pyridine (200 mg, 0.673 mmol) in ethanol (6 mL) and water (2 mL) was added ammonium chloride (17.99 mg, 0.336 mmol) and iron powder (113 mg, 2.018 mmol). The reaction mixture was heated at reflux under nitrogen for 1 hour. The reaction mixture was filtered through a pad of celite and the pad washed with ethyl acetate. The combined filtrate and washings were separated between ethyl acetate and saturated sodium bicarbonate. The organic phase was washed with water and brine, then dried over magnesium sulphate and evaporated in vacuo to give the title product (153 mg) as a pale brown gum. LCMS (2 min, formic) Rt 0.35 min, m/z (ES+) 268 (M+H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux under nitrogen for 1 hour
  3. filtrationThe reaction mixture was filtered through a pad of celite
  4. washthe pad washed with 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 and brine
  7. dry with materialdried over magnesium sulphate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-e6fe773a0635408fabe2f06cc27fdaee
Source dataset
uspto-grants-2016_01
Patent number
US09242972B2

Reaction notes

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