Acetic Acid → 2-Bromo-7-hydroxy-3-(3-methyl-2-buten-1-yl)-3,5,6,7-tetrahydro-imidazo[4,5-c]pyridin-4-one

HRID 230106Notes

Reaction equation

HRID 230106 reaction equation
O.[Br:2][C:3]1[N:7]([CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])[C:6]([C:13](OC)=[O:14])=[C:5]([CH:17]([OH:22])[CH2:18][N+:19]([O-])=O)[N:4]=1.C(O)(=O)C>C(O)C.[Fe]>[Br:2][C:3]1[N:7]([CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])[C:6]2[C:13](=[O:14])[NH:19][CH2:18][CH:17]([OH:22])[C:5]=2[N:4]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 67435131Methyl 2-bromo-5-(1-hydroxy-2-nitro-ethyl)-3-(3-methyl-2-buten-1-yl)-3H-imidazole-4-carboxylate

Product 1

HCID 674358652-Bromo-7-hydroxy-3-(3-methyl-2-buten-1-yl)-3,5,6,7-tetrahydro-imidazo[4,5-c]pyridin-4-one

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

90 ml of water and 5.40 g iron powder are added to 4.15 g methyl 2-bromo-5-(1-hydroxy-2-nitro-ethyl)-3-(3-methyl-2-buten-1-yl)-3H-imidazole-4-carboxylate in 270 ml of ethanol. The mixture is refluxed, combined with 36 ml glacial acetic acid and stirred for one and a half hours at reflux temperature. The cooled reaction solution is filtered through Celite. The filtrate is evaporated down, combined with ethanol and made basic with solid potassium carbonate. The mixture is stirred for three hours at 60° C. Then the ethanol is distilled off, the flask residue is combined with water and extracted with ethyl acetate. The combined extracts are dried over magnesium sulphate and evaporated down. The crude product is purified by chromatography over a silica gel column with methylene chloride/methanol (1:1 to 7:1) as eluant.

Workup

  1. temperatureThe mixture is refluxed
  2. temperatureat reflux temperature
  3. customThe cooled reaction solution
  4. filtrationis filtered through Celite
  5. customThe filtrate is evaporated down
  6. stirringThe mixture is stirred for three hours at 60° C
  7. distillationThen the ethanol is distilled off
  8. extractionextracted with ethyl acetate
  9. dry with materialThe combined extracts are dried over magnesium sulphate
  10. customevaporated down
  11. customThe crude product is purified by chromatography over a silica gel column with methylene chloride/methanol (1:1 to 7:1) as eluant

Sources & evidence

ORD record
ord-c998851b96fd44ca9575b717c21191b8
Source dataset
uspto-grants-2009_07
Patent number
US07566707B2

Reaction notes

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