HCID 178470334, compound → 1H-Imidazole-4-carboxylic acid, 5-amino-1-methyl-, ethyl ester

HRID 1728342Notes

Reaction equation

HRID 1728342 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[C:5](S)=[N:4][C:3]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10]>[Ni].C(O)C>[NH2:1][C:2]1[N:6]([CH3:7])[CH:5]=[N:4][C:3]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

4

Reactant 1

HCID 178470334HCID 178470334, compound

Product 1

HCID 5359001H-Imidazole-4-carboxylic acid, 5-amino-1-methyl-, ethyl esterYield 96%

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 702EthanolSolvent

Procedure

A solution of ethyl 5-amino-2-mercapto-1-methylimidazole-4-carboxylate (1.0 g, 5.0 mmol), prepared by the method of Cook, Downer, and Heilbron, J. Chem. Soc. 2028.(1948), and W-2 Raney nickel (2 mL, 50% slurry in water)in ethanol (20 mL) were agitated in an ultrasonic cleaning bath at 50° C. for 1 hour. Sonication was continued for an additional 2 hours at 55° C. adding additional Raney nickel (ca 2 mL, 50% in water) every hour. Filtration followed by evaporation under reduced pressure afforded 0.81 g (96%) of the title compound as a tan crystalline solid which was used without further purification. m.p. 193°-194° C. TLC (10% methanol/90% ethyl acetate) Rf =0.19. 1H NMR (CDCl3, 300 MHz) d 1.39 (t, 3H), 3.46 (s, 3H), 4.34 (q, 2H), 4.75-4.95 (br, 2H), 7.01 (s, 1H). MS (DCl/NH3) m/e 170 (M+H)+. Anal calcd for C7H11N3O2.0.20 H2O: C, 48.66; H, 6.65; N, 24.32. Found: C, 48.98; H, 6.54; N, 24.12.

Workup

  1. customSonication
  2. filtrationFiltration
  3. customfollowed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-6a84d55ef6834ece8f2eaac75ce19fba
Source dataset
uspto-grants-1994_07
Patent number
US05326776

Reaction notes

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