Hydrazine hydrate (1:1) → 2-Hydrazonomethyl-5-morpholin-4-yl-phenol

HRID 349686

Reaction equation

HRID 349686 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:7]=[CH:6][C:3]=1[CH:4]=O.O.[NH2:17][NH2:18]>N1C=CC=CC=1>[N:17](=[CH:4][C:3]1[CH:6]=[CH:7][C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:9][C:2]=1[OH:1])[NH2:18]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 98156592-Hydroxy-4-morpholin-4-yl-benzaldehyde

Product 1

HCID 1363432492-Hydrazonomethyl-5-morpholin-4-yl-phenolYield 67%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-hydroxy-4-morpholin-4-yl-benzaldehyde (0.135 g, 0.65 mmol) in pyridine (5 mL) was treated with hydrazine hydrate (33 mg, 0.65 mmol) and stirred for 3 h at room temperature. The reaction mixture was concentrated in vacuo and the residue was partitioned between EtOAc and 5% sodium bicarbonate. The organic layer was dried over Na2SO4 and concentrated in vacuo to afford the product as a pale yellow solid (96 mg, 67%)

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between EtOAc and 5% sodium bicarbonate
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-671878f9dfe749a1bb6e0c3e89d3bdc2
Source dataset
uspto-grants-2007_02
Patent number
US07179912B2

Linked notes

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