Hydrochloric Acid → HCID 15623003, compound

HRID 330371Notes

Reaction equation

HRID 330371 reaction equation
[C:1]([C:9]1[N:13]2[CH2:14][CH2:15][CH:16]([C:17]([OH:19])=[O:18])[C:12]2=[C:11](Br)[N:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[O-2].[Mg+2].[H][H].Cl>O.CO.[Pd].O>[C:1]([C:9]1[N:13]2[CH2:14][CH2:15][CH:16]([C:17]([OH:19])=[O:18])[C:12]2=[CH:11][N:10]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 6850729Magnesium monoxideHCID 15623002HCID 15623002, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15623003HCID 15623003, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

Three (3) grams of 3-benzoyl-1-bromo-6,7-dihydro-5H-pyrrolo[1,2-c]imidazole-7-carboxylic acid were dissolved in 200 ml of a 50% water/methanol mixed liquid, containing 0.7 g of sodium hydroxide incorporated with 1.5 g of magnesium oxide and 0.6 g of 5% palladium/carbon and then agitated to the extent that absorption of the hydrogen gas is stopped (about 4 hours). After the end of the reaction, the reaction mixture was filtered and washed several times with water and methanol. The filtrate was concentrated under a reduced pressure and washed twice with about 70 ml of ethyl acetate. The aqueous layer obtained was made weakly acidic with conc. hydrochloric acid to precipitate crystals which were then filtered off. The rough crystals obtained were water washed, air-dried and then recrystallized from ethanol to obtain 2.1 g of 3-benzoyl-6,7-dihydro-5H-pyrrolo[1,2-c]imidazole-7-carboxylic acid.

Workup

  1. custom(about 4 hours)
  2. customAfter the end of the reaction
  3. filtrationthe reaction mixture was filtered
  4. washwashed several times with water and methanol
  5. concentrationThe filtrate was concentrated under a reduced pressure
  6. washwashed twice with about 70 ml of ethyl acetate
  7. customThe aqueous layer obtained
  8. customto precipitate crystals which
  9. filtrationwere then filtered off
  10. customThe rough crystals obtained
  11. washwashed
  12. customair-dried
  13. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-a51e728229e648529a839b6a907f5976
Source dataset
uspto-grants-1990_01
Patent number
US04895956

Reaction notes

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