Hydrazine hydrate (1:1) → HCID 15662659, compound

HRID 1585101Notes

Reaction equation

HRID 1585101 reaction equation
C1(=O)[N:5]([O:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2/[C:14](=[CH:19]\[O:20][CH3:21])/[C:15]([O:17][CH3:18])=[O:16])C(=O)C2=CC=CC=C12.O.NN>CO.C(OCC)C>[NH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1/[C:14](=[CH:19]\[O:20][CH3:21])/[C:15]([O:17][CH3:18])=[O:16]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 15662656HCID 15662656, compound

Product 1

HCID 15662659HCID 15662659, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

(E)-methyl 2-[phthalimidooxymethylphenyl]-3-methoxypropenoate (1.11 g, 3.02 mmol) (prepared as described in Example 4 of EP 0463488) was suspended in methanol (25 ml) at room temperature and hydrazine hydrate (0.151 g, 3.02 mmol) was added. The resulting solution was stirred for 3 hours. The white precipitate which formed was filtered off and the solvent removed to give a white semi-solid. This was diluted with diethyl ether, and the white solid filtered off to give (E)-methyl 2-[2-aminooxymethylphenyl]-3 -methoxypropenoate (93%) as a yellow oil which was used immediately in the next stage without further purification.

Workup

  1. customThe white precipitate which formed
  2. filtrationwas filtered off
  3. customthe solvent removed
  4. customto give a white semi-solid
  5. filtrationthe white solid filtered off

Sources & evidence

ORD record
ord-0abc0971e51941a99b0d99f1b51d7ef1
Source dataset
uspto-grants-1999_08
Patent number
US05935999

Reaction notes

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