Pyridine → 2-[(5-Ethoxycarbonylmethoxy-1,2,3,4-tetrahydro-1-naphthyl)methoxycarbonyl]-1,1-diphenylhydrazine

HRID 344060

Reaction equation

HRID 344060 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH2:5]([O:7][C:8]([CH2:10][O:11][C:12]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[CH2:14][CH2:15][CH2:16][CH:17]2[CH2:22][OH:23])=[O:9])[CH3:6].N1C=CC=CC=1.Cl.[C:31]1([N:37]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[NH2:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(Cl)Cl>[CH2:5]([O:7][C:8]([CH2:10][O:11][C:12]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[CH2:14][CH2:15][CH2:16][CH:17]2[CH2:22][O:23][C:1]([NH:38][N:37]([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:2])=[O:9])[CH3:6]

Participants

6

Reactant 4

HCID 1049Pyridine2×HCID 6371PhosgeneHCID 10738Hydrazine, 1,1-diphenyl-, hydrochloride (1:1)HCID 53647005(5-Ethoxycarbonylmethoxy-1,2,3,4-tetrahydro-1-naphthyl)methanol

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a methylene chloride solution (1 ml) of phosgene dimer (0.027 ml) was added a methylene chloride solution (2 ml) of (5-ethoxycarbonylmethoxy-1,2,3,4-tetrahydro-1-naphthyl)methanol (0.12 g) and pyridine (0.1 ml) at -5° C., and the solution was stirred at room temperature for two hours. To the reaction mixture was added a solution of 1,1-diphenylhydrazine hydrochloride (0.10 g) and pyridine (0.05 ml) in methylene chloride (2 ml). The solution was stirred at room temperature for 3 hours, washed with 5% hydrochloric acid, water, and brine, dried over sodium sulfate, and evaporated in vacuo. The residue was chromatographed (n-hexane-ethyl acetate) over silica gel to afford 2-[(5-ethoxycarbonylmethoxy-1,2,3,4-tetrahydro-1-naphthyl)methoxycarbonyl]-1,1-diphenyihydrazine (0.13 g) as colorless solids.

Workup

  1. stirringThe solution was stirred at room temperature for 3 hours
  2. washwashed with 5% hydrochloric acid, water, and brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed (n-hexane-ethyl acetate) over silica gel

Sources & evidence

ORD record
ord-5434fa9b16764b019f4f78cd116bcaef
Source dataset
uspto-grants-1999_01
Patent number
US05863918

Linked notes

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