Acetic Acid → HCID 67083765, compound

HRID 2239522Notes

Reaction equation

HRID 2239522 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[N:4][C:3]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17].C(O)C.[F:24][C:25]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:26]=1[NH2:27].C(O)(=O)C>N>[F:24][C:25]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:26]=1[NH:27][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[N:4][C:3]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 97092,4-DifluoroanilineHCID 67083777HCID 67083777, compound

Product 1

HCID 67083765HCID 67083765, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Conditions

Temperature
75 °C

Procedure

To a 50 mL round bottom flask charged with a magnetic stir bar and ethyl 4-chloro-6,7-dimethoxycinnoline-3-carboxylate (0.200 g, 0.675 mmol) (Method 7) was added anhydrous ethanol (10 mL), 2,4-difluoroaniline (0.087 g, 0.675 mmol), and glacial acetic acid (˜100 μL). The reaction mixture was then heated to 75° C. for 1 h, cooled to rt, and diluted with concentrated aqueous ammonia (˜5 mL). The crude product precipitated from this reaction mixture and was collected via vacuum filtration using a Buchner funnel. The solid was washed water (1×100 mL) and diethyl ether (1×100 mL) to yield the crude product which was purified on 40 g silica using EtOAc as eluent providing 0.231 g (88%) of the title compound as a yellow solid. 1H NMR: 9.25 (s, 1H), 7.70 (s, 1H), 7.50 (s, 1H), 7.40 (m, 1H), 7.30 (m, 1H), 7.10 (m, 1H), 4.02 (s, 3H), 3.95 (q, 2H), 3.85 (s, 3H), 1.20 (t, 3H); m/z 390.

Workup

  1. additionTo a 50 mL round bottom flask charged with a magnetic stir bar
  2. temperaturecooled to rt
  3. customThe crude product precipitated from this reaction mixture
  4. filtrationwas collected via vacuum filtration
  5. washThe solid was washed water (1×100 mL) and diethyl ether (1×100 mL)
  6. customto yield the crude product which
  7. customwas purified on 40 g silica

Sources & evidence

ORD record
ord-77b1157484954031853e3a55d61580a3
Source dataset
uspto-grants-2010_05
Patent number
US07723337B2

Reaction notes

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