Formic Acid → Acetic-formic anhydride

HRID 547628Notes

Reaction equation

HRID 547628 reaction equation
[CH:1](O)=[O:2].[C:4]([O:7][C:8](=[O:10])C)(=[O:6])[CH3:5].C(N(C(C)C)CC)(C)C.[O:20]1[CH2:24][CH2:23][O:22][CH:21]1[C:25]1[CH:30]=[CH:29][C:28]([O:31][C:32]2[CH:38]=[CH:37][C:35]([NH2:36])=[C:34]([N+:39]([O-:41])=[O:40])[CH:33]=2)=[C:27]([O:42][CH3:43])[CH:26]=1.C(OC=O)(=O)C>C(OCC)(=O)C.O1CCCC1>[C:4]([O:7][CH:8]=[O:10])(=[O:6])[CH3:5].[O:20]1[CH2:24][CH2:23][O:22][CH:21]1[C:25]1[CH:30]=[CH:29][C:28]([O:31][C:32]2[CH:38]=[CH:37][C:35]([NH:36][CH:1]=[O:2])=[C:34]([N+:39]([O-:41])=[O:40])[CH:33]=2)=[C:27]([O:42][CH3:43])[CH:26]=1

Participants

9

Reactant 5

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 75269Acetic-formic anhydrideHCID 81531DiisopropylethylamineHCID 575859654-{[4-(1,3-Dioxolan-2-yl)-2-(methyloxy)phenyl]oxy}-2-nitroaniline

Product 2

HCID 75269Acetic-formic anhydrideHCID 57585943(4-{[4-(1,3-Dioxolan-2-yl)-2-(methyloxy)phenyl]oxy}-2-nitrophenyl)formamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Formic acetic anhydride was prepared by adding 96% formic acid (0.702 ml, 18.3 mmol) to acetic anhydride (0.863 ml, 9.1 mmol) and stirring for 30 minutes. A tetrahydrofuran solution of diisopropylethylamine (3.2 ml, 18.3 mmol) and 4-{[4-(1,3-dioxolan-2-yl)-2-(methyloxy) phenyl]oxy}-2-nitroaniline (2.53 g, 7.62 mmol) was added to the formic acetic anhydride. The reaction was stirred for approximately 18 hours. The reaction mixture was diluted with ethyl acetate and washed with 1N NaOH. The organic layers were dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography to give (4-{[4-(1,3-dioxolan-2-yl)-2-(methyloxy)phenyl]oxy}-2-nitrophenyl) formamide. (M+1) 360.8, 2.31 min (LC/MS method B)

Workup

  1. stirringThe reaction was stirred for approximately 18 hours
  2. washwashed with 1N NaOH
  3. dry with materialThe organic layers were dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3b35c4d748fe4e42bf3b97ec01cecd05
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

Loading…