Formic Acid → HCID 89543743, compound

HRID 509452Notes

Reaction equation

HRID 509452 reaction equation
[CH:1]([OH:3])=O.C(OC(=O)C)(=O)C.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:22]3[CH2:23][CH2:24][CH2:25][C:26](=[O:27])[C:21]=3[O:20][N:19]=2)=[CH:14][C:13]=1[O:28][CH3:29]>C1COCC1>[CH3:29][O:28][C:13]1[CH:14]=[C:15]([C:18]2[C:22]3[CH2:23][CH2:24][CH2:25][C:26](=[O:27])[C:21]=3[O:20][N:19]=2)[CH:16]=[CH:17][C:12]=1[NH:11][CH:1]=[O:3]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 89543725HCID 89543725, compound

Product 1

HCID 89543743HCID 89543743, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To formic acid (6.24 g, 135.6 mmol) was added dropwise 3.96 g (38.8 mmol) of acetic anhydride (exothermic, cooling with tap water was used). The reaction mixture was stirred for 1 hr. The resulting mixture was transferred via cannula into another reaction flask containing a solution of 3-(4-amino-3-methoxyphenyl)-5,6-dihydrobenzo[d]isoxazol-7(4H)-one in 50 ml of THF (Cooling with tap water was used). The mixture was stirred for 2 hr, extracted with DCM, washed with water and brine, dried over sodium sulfate and concentrated to furnish 2.65 g of the title compound, MS(M+H)+=287.

Workup

  1. customThe resulting mixture was transferred via cannula into another reaction flask
  2. stirringThe mixture was stirred for 2 hr
  3. extractionextracted with DCM
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4f8d438492094e9bba1a427633bad510
Source dataset
uspto-grants-2015_08
Patent number
US09096582B2

Reaction notes

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