Acetic Anhydride → HCID 10988583, compound

HRID 1370323Notes

Reaction equation

HRID 1370323 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([O:14][CH3:15])[CH:8]=[CH:9][C:10]=2[O:12][CH3:13])[N:5]=[CH:4][CH:3]=1.[C:16](OC(=O)C)(=[O:18])[CH3:17]>CN(C1C=CN=CC=1)C>[C:16]([NH:1][C:2]1[C:11]2[C:6](=[C:7]([O:14][CH3:15])[CH:8]=[CH:9][C:10]=2[O:12][CH3:13])[N:5]=[CH:4][CH:3]=1)(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 10867424HCID 10867424, compound

Product 1

HCID 10988583HCID 10988583, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A suspension of 3 g (14.7 mmol) of 4-amino-5,8-dimethoxyquinoline and of 0.72 g (5.88 mmol) of DMAP in 30 mL of acetic anhydride is stirred at ambient temperature for 24 hours. After concentrating on a rotary evaporator, the reaction medium is washed with 40 mL of saturated NaHCO3 solution and then extracted with CHCl3 (3 times 50 mL). The extracts are dried over MgSO4 and the solvent is evaporated off, followed by evaporation of the remaining acetic anhydride by azeotropic entrainment with benzene. 2.7 g of the expected derivative are obtained in the form of a yellow powder.

Workup

  1. concentrationAfter concentrating on a rotary evaporator
  2. washthe reaction medium is washed with 40 mL of saturated NaHCO3 solution
  3. extractionextracted with CHCl3 (3 times 50 mL)
  4. dry with materialThe extracts are dried over MgSO4
  5. customthe solvent is evaporated off
  6. customfollowed by evaporation of the remaining acetic anhydride by azeotropic entrainment with benzene
  7. custom2.7 g of the expected derivative are obtained in the form of a yellow powder

Sources & evidence

ORD record
ord-6b67afcbfcd144c78e00755b5df41971
Source dataset
uspto-grants-2003_06
Patent number
US06583150B1

Reaction notes

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