Hydrazine hydrate (1:1) → 2-Pyridinamine, 6-[(aminooxy)methyl]-

HRID 1914610Notes

Reaction equation

HRID 1914610 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[O:12][CH2:13][C:14]1[N:19]=[C:18]([N:20]2C(=O)C3C(=CC=CC=3)C2=O)[CH:17]=[CH:16][CH:15]=1.O.NN>C1COCC1>[NH2:3][O:12][CH2:13][C:14]1[N:19]=[C:18]([NH2:20])[CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 670751742-(6-{[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]methyl}pyridin-2-yl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 450795102-Pyridinamine, 6-[(aminooxy)methyl]-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(6-{[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]methyl}pyridin-2-yl)-1H-isoindole-1,3(2H)-dione (50 g, 125 mmol) in THF (350 mL) was added dropwise hydrazine hydrate (61 mL, 1.25 mol) at room temperature. After stirring overnight at room temperature, the reaction mixture was filtered and the filtrate was concentrated to dryness in vacuo. Purification of the residue on silica gel afforded 6-[(aminooxy)methyl]pyridin-2-amine as a colourless oil [10.0 g; 57% of theory; HPLC/MS: m/z=140 (M+H); log P(HCOOH)<−0.23].

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated to dryness in vacuo
  3. customPurification of the residue on silica gel

Sources & evidence

ORD record
ord-a42b3f71fefe40b99337e8ea7a4e9ecd
Source dataset
uspto-grants-2013_12
Patent number
US08614217B2

Reaction notes

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