Acetic Anhydride → 8-Nitro-2-(3-(trifluoromethyl)phenyl)quinolin-4-yl acetate

HRID 520461Notes

Reaction equation

HRID 520461 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[NH:12][C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=1)=[CH:10][C:9]2=[O:24])([O-:3])=[O:2].C(N(CC)CC)C.[CH3:32][C:33](OC(C)=O)=[O:34].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:33]([O:24][C:9]1[C:8]2[C:13](=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][CH:7]=2)[N:12]=[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:21])[F:22])[CH:15]=2)[CH:10]=1)(=[O:34])[CH3:32]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 585529228-nitro-2-(3-(trifluoromethyl)phenyl)quinolin-4(1H)-one

Product 1

HCID 585528568-Nitro-2-(3-(trifluoromethyl)phenyl)quinolin-4-yl acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 8-nitro-2-(3-(trifluoromethyl)phenyl)quinolin-4(1H)-one 37 (707 mg, 2.11 mmol), triethylamine (1 mL), and Ac2O (0.7 mL) in CH2Cl2 (10 mL) was stirred at room temperature for 16 h. Sat. aq NaHCO3 (10 mL) was added, and the reaction extracted with CH2Cl2. The combined organic layers were dried (MgSO4) and concentrated to give 38.

Workup

  1. extractionthe reaction extracted with CH2Cl2
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a2d89c3bf66c4a74b48425fa29bee2a5
Source dataset
uspto-grants-2016_05
Patent number
US09326986B2

Reaction notes

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