Carbon Dioxide → n-Propyl Cinnoline-4-carboxylate

HRID 255852ノート

反応式

HRID 255852 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 20164604n-Propyl Cinnoline-4-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e63f5621c93e4a72858163153f30ce58
出典データセット
uspto-grants-1987_10
特許番号
US04699651

反応ノート

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