Water → HCID 19829823, compound

HRID 1493607Notes

Reaction equation

HRID 1493607 reaction equation
C[O-].[Na+].[NH2:4][C:5]([NH:7][N:8]([CH2:16][C:17]([O:19]C)=O)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=1)=[O:6].O.P([O-])([O-])([O-])=O>CO>[CH3:15][C:11]1[CH:10]=[C:9]([N:8]2[CH2:16][C:17](=[O:19])[NH:4][C:5](=[O:6])[NH:7]2)[CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1061PhosphateHCID 10942334Sodium MethoxideHCID 54374596HCID 54374596, compound

Product 1

HCID 19829823HCID 19829823, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of sodium methoxide (2.17M in methanol; 3 ml) was added to a stirred solution of methyl [2-(aminocarbonyl)-1-(3-methylphenyl)hydrazino]acetate (0.5 g) in methanol (1 ml), and the mixture was stirred at 20° for 1.0 h. Water (20 ml) was added, followed by pH 6.5 phosphate buffer solution (30 ml), and the mixture was extracted with ethyl acetate (3×80 ml). The combined extracts were washed with water (2×80 ml) and saturated brine (80 ml), dried, and evaporated in vacuo to give a solid which was triturated with ether (30 ml) to give the title compound (261 mg), m.p. 245°-247°.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×80 ml)
  2. washThe combined extracts were washed with water (2×80 ml) and saturated brine (80 ml)
  3. customdried
  4. customevaporated in vacuo
  5. customto give a solid which
  6. customwas triturated with ether (30 ml)

Sources & evidence

ORD record
ord-a17f02a62d71495282065d1f3c3a983f
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Reaction notes

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