Cyanoacetic acid hydrazide → 2-Formyl-3-methylquinoxaline-1,4-dioxide cyanoacetylhydrazone

HRID 28112Notes

Reaction equation

HRID 28112 reaction equation
[CH:1]([C:3]1[C:12]([CH3:13])=[N+:11]([O-:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N+:4]=1[O-:15])=O.[C:16]([CH2:18][C:19]([NH:21][NH2:22])=[O:20])#[N:17]>C(O)C>[C:16]([CH2:18][C:19]([NH:21][N:22]=[CH:1][C:3]1[C:12]([CH3:13])=[N+:11]([O-:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N+:4]=1[O-:15])=[O:20])#[N:17]

Participants

4

Reactant 2

HCID 8820Cyanoacetic acid hydrazideHCID 178429580HCID 178429580, compound

Product 1

HCID 1363356282-Formyl-3-methylquinoxaline-1,4-dioxide cyanoacetylhydrazone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension comprising 20.4 grams (0.1 mole) of 2-formyl-3-methylquinoxaline-1,4-dioxide (m.p. of 180°-182° C.) and 9.9 grams (0.1 mole) of cyanoacetylhydrazine in 200 ml of ethanol was stirred for 4 hours at room temperature. The separated product was sucked off and washed with ethanol, so yielding 22.2 grams (78% of theoretical) of crude material. Upon crystallization from dimethylformamide, yellow crystals melting at a temperature within the range of 255°-260° C. were obtained.

Workup

  1. washwashed with ethanol
  2. customso yielding 22.2 grams (78% of theoretical) of crude material
  3. customUpon crystallization from dimethylformamide, yellow crystals
  4. custommelting at a temperature within the range of 255°-260° C.
  5. customwere obtained

Sources & evidence

ORD record
ord-ef9eb593a3cb44209c26cba25235065f
Source dataset
uspto-grants-1980_09
Patent number
US04225604

Reaction notes

Loading…