Formic Acid → HCID 18790582, compound

HRID 1106983Notes

Reaction equation

HRID 1106983 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:14](=[O:27])[CH2:15][S:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=[CH:19][CH:18]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH:11]1[O:13][CH2:12]1.C(O)=[O:29]>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:14](=[O:27])[CH2:15][S:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=[CH:19][CH:18]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH:11]([OH:13])[CH2:12][OH:29]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 18790505HCID 18790505, compound2×

Product 1

HCID 18790582HCID 18790582, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-[2-[3-Methoxy-4-(2,3-epoxypropoxy)phenyl]-2-oxoethylthio]quinoline (Compound 57; 2.0 g, 5.25 mmol) was added at 0° C. to the mixture of formic acid (40 ml) and water (4 ml), and stirred at room temperature overnight. The solvent was removed under reduced pressure. The residue was added with an ice-cooled aqueous solution of 40% sodium hydroxide (7.0 ml) and stirred at 0° C. for 30 minutes. The solvent was removed under reduced pressure and the residue was chromatographed by silica gel column chromatography (dichloromethane:methanol=20:1) to obtain 1.4 g of the titled compound (67.0%). Melting Point: 177° C. (decomp.)

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionThe residue was added with an ice-
  3. temperaturecooled aqueous solution of 40% sodium hydroxide (7.0 ml)
  4. stirringstirred at 0° C. for 30 minutes
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was chromatographed by silica gel column chromatography (dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-d3b9a27b6be04d4993c6ececbf8f3bd3
Source dataset
uspto-grants-2000_05
Patent number
US06057447

Reaction notes

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