Sodium Hydroxide → 2-[(5-Carboxymethoxy-1,2,3,4-tetrahydro-1-naphthyl)methoxycarbonyl]-1,1-diphenylhydrazine

HRID 344066Notes

Reaction equation

HRID 344066 reaction equation
C([O:3][C:4]([CH2:6][O:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][CH2:12][CH:13]2[CH2:18][O:19][C:20]([NH:22][N:23]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])=[O:5])C.[OH-].[Na+]>O1CCOCC1>[C:4]([CH2:6][O:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][CH2:12][CH:13]2[CH2:18][O:19][C:20]([NH:22][N:23]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:21])([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 701873142-[(5-Ethoxycarbonylmethoxy-1,2,3,4-tetrahydro-1-naphthyl)methoxycarbonyl]-1,1-diphenylhydrazine

Product 1

HCID 701875302-[(5-Carboxymethoxy-1,2,3,4-tetrahydro-1-naphthyl)methoxycarbonyl]-1,1-diphenylhydrazineYield 50%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-[(5-ethoxycarbonylmethoxy-1,2,3,4-tetrahydro-1-naphthyl)methoxycarbonyl]-1,1-diphenylhydrazine (0.17 g) and 1N-aqueous sodium hydroxide (1 ml) in dioxane (1.5 ml) was stirred at room temperature for 30 minutes and partitioned between 5% hydrochloric acid and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and evaporated in vacuo. The residue was washed with isopropanol to afford 2-[(5-carboxymethoxy-1,2,3,4-tetrahydro-1-naphthyl)-methoxycarbonyl]-1,1-diphenylhydrazine (0.08 g) as a colorless powder.

Workup

  1. custompartitioned between 5% hydrochloric acid and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. washThe residue was washed with isopropanol

Sources & evidence

ORD record
ord-9934218a01434cf79ad1921acebabe5d
Source dataset
uspto-grants-1999_01
Patent number
US05863918

Reaction notes

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