Acetic Anhydride → HCID 21998724, compound

HRID 1976790Notes

Reaction equation

HRID 1976790 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[NH:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6].[C:14](OC(=O)C)(=[O:16])[CH3:15].C([O-])(O)=O.[Na+]>ClCCl>[C:14]([NH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[NH:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6])(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 15586064Methyl 3-amino-4-(methylamino)benzoate

Product 1

HCID 21998724HCID 21998724, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 75A (1.80 g, 10.0 mmol) in dichloromethane (100 mL) was treated sequentially with acetic anhydride (3.06 g, 30.0 mmol) and 10% NaHCO3 (100 mL) and stirred for 30 minutes. The organic layer was separated, washed with brine (30 mL), dried (MgSO4), filtered, concentrated until solid precipitated, treated with diethyl ether, and filtered to provide 1.66 g of desired product.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated until solid
  6. customprecipitated
  7. additiontreated with diethyl ether
  8. filtrationfiltered

Sources & evidence

ORD record
ord-11a4a04320d64420bb683d0d510368fa
Source dataset
uspto-grants-2001_05
Patent number
US06228868B1

Reaction notes

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