Formic Acid → HCID 19830064, compound

HRID 1493575Notes

Reaction equation

HRID 1493575 reaction equation
[CH:1]([OH:3])=[O:2].[C:4](N1C=CN=C1)(N1C=CN=C1)=[O:5].CI.O[C:19]1[CH:28]=[C:27]2[C:22]([C:23]3[O:32][C:31]4[CH:33]=[C:34]([OH:37])[CH:35]=[CH:36][C:30]=4[C:24]=3[C:25](=[O:29])[NH:26]2)=[CH:21][CH:20]=1>C(Cl)(Cl)Cl.CN(C)C=O.O>[CH:1]([O:3][C:19]1[CH:28]=[C:27]2[C:22]([C:23]3[O:32][C:31]4[CH:33]=[C:34]([O:37][CH:4]=[O:5])[CH:35]=[CH:36][C:30]=4[C:24]=3[C:25](=[O:29])[NH:26]2)=[CH:21][CH:20]=1)=[O:2]

Participants

8

Reactant 4

HCID 284Formic AcidHCID 6328Methyl iodideHCID 682631,1'-CarbonyldiimidazoleHCID 10061491HCID 10061491, compound

Product 1

HCID 19830064HCID 19830064, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.35 ml of formic acid in 10 ml of dry chloroform were added 1.5 g of 1,1'-carbonyldiimidazole and 1.74 ml of methyl iodide, and the mixture was stirred at room temperature for 2.5 hours. To the reaction mixture was added a solution of 0.5 g of 3,9-dihydroxy-5H-benzofuro[3,2-c]quinolin-6-one in 10 ml of dry N,N-dimethylformamide, and the mixture was stirred overnight at room temperature. To the reaction mixture was added 30 ml of water, and the precipitates were collected by filtration, washed with ethyl acetate, and dried at 60° C under reduced pressure to obtain 0.54 g of 3,9-bis(formyloxy)-5H-benzofuro[3,2-c]quinolin-6-one.

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. filtrationthe precipitates were collected by filtration
  3. washwashed with ethyl acetate
  4. customdried at 60° C under reduced pressure

Sources & evidence

ORD record
ord-87c5a0f36d074f1599a5eb66a3692a48
Source dataset
uspto-grants-1991_06
Patent number
US05023261

Reaction notes

Loading…