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

HRID 594111Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 594111
[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

Komponenten

6

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e6fe773a0635408fabe2f06cc27fdaee
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242972B2

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