Carbon Dioxide → n-Propyl Cinnoline-4-carboxylate

HRID 255852Notes

Reaction equation

HRID 255852 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([OH:13])=[O:12])=[CH:3][N:2]=1.C(N1[CH:25]=[CH:24]N=C1)(N1C=CN=C1)=O.[C:26](=O)=O.N1C=CN=C1.[Na]>O1CCCC1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([O:13][CH2:26][CH2:24][CH3:25])=[O:12])=[CH:3][N:2]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 682631,1'-CarbonyldiimidazoleHCID 89099Cinnoline-4-carboxylic acidHCID 57373095Imidazole sodium

Product 1

HCID 20164604n-Propyl Cinnoline-4-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 870 mg of 1, and 850 mg of carbonyidimidazole (CDII) in 30 ml of tetrahydrofuran (THF) was stirred at room temperature until CO2 evolution ceased (ca. 30 minutes). After being stirred for 2 hours, the resulting mixture was treated with 320 mg of dry nypropanol and 3 drops of a 0.1 M solution of sodium imidazole in THE. The mixture was held at room temperature overnight, then the solvent was evaporated and the residue was partitioned between water and ether. The etheral extract was washed with saturated sodium bicarbonate solution, then with brine, then dried (MgSO4) and stripped in a rotary evaporator. The residue was chromatographed over silica gel, using a 1:1 v:v mixture of cyclohexane and ethyl acetate as eluent, to give 5, as a yellow oil.

Workup

  1. custom(ca. 30 minutes)
  2. waitThe mixture was held at room temperature overnight
  3. customthe solvent was evaporated
  4. customthe residue was partitioned between water and ether
  5. extractionThe etheral extract
  6. washwas washed with saturated sodium bicarbonate solution
  7. dry with materialwith brine, then dried (MgSO4)
  8. customstripped in a rotary evaporator
  9. customThe residue was chromatographed over silica gel
  10. additionv mixture of cyclohexane and ethyl acetate as eluent
  11. customto give 5

Sources & evidence

ORD record
ord-e63f5621c93e4a72858163153f30ce58
Source dataset
uspto-grants-1987_10
Patent number
US04699651

Reaction notes

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