1,1-Dimethylhydrazine → HCID 86748126, compound

HRID 2225865Notes

Reaction equation

HRID 2225865 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][O:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)=[CH:7][CH:6]=1.[CH3:27][N:28]([CH3:30])[NH2:29]>CO.O1CCCC1.C(O)(=O)C>[CH3:1][O:2][C:3](=[O:26])/[C:4](=[N:29]/[N:28]([CH3:30])[CH3:27])/[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][O:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 2

HCID 59761,1-DimethylhydrazineHCID 541704664-[2-(2-Naphthalenyloxy)ethoxy]-alpha-oxobenzeneacetic acid methyl ester

Product 1

HCID 86748126HCID 86748126, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-[2-(2-naphthalenyloxy)ethoxy]-alpha-oxobenzeneacetic acid methyl ester (3.5 g), 1,1-dimethylhydrazine (2.28 mL) in methanol (40 mL), tetrahydrofuran (20 mL) and one drop of glacial acetic acid was refluxed for 48 hours and evaporated to dryness. The crude mixture was separated by HPLC (dichloromethane-ether, 49:1) and the more polar component was crystallized from dichloromethane-methanol to provide 0.9 g of (E)-alpha-(dimethylhydrazono)-4-[2-(2-naphthalenyloxy)ethoxy]benzeneacetic acid methyl ester as a colorless solid, mp 137°-138° C.

Workup

  1. temperaturewas refluxed for 48 hours
  2. customevaporated to dryness
  3. customThe crude mixture was separated by HPLC (dichloromethane-ether, 49:1)
  4. customthe more polar component was crystallized from dichloromethane-methanol

Sources & evidence

ORD record
ord-02a3c1e893b44951a558f8271d521e77
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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