Trifluoroacetic acid → HCID 12210169, compound

HRID 595032Notes

Reaction equation

HRID 595032 reaction equation
[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:13](OC(=O)C)(=O)[CH3:14].C(O)(C(F)(F)F)=O>O.CO>[CH3:12][O:11][C:10]1[C:2]2[N:1]=[C:13]([CH3:14])[O:5][C:4](=[O:6])[C:3]=2[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7918Acetic AnhydrideHCID 2557202-Amino-3-methoxybenzoic acid

Product 1

HCID 12210169HCID 12210169, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
140 °C

Procedure

2-Amino-3-methoxybenzoic acid (10.1 g, 60.4 mmol) was suspended in acetic anhydride (50 ml, 530 mmol). The mixture was heated to 140° C. with stirring for 180 min. The reaction mixture was cooled to room temperature and concentrated to provide Intermediate A18A (11.51 g, 100%): HPLC: RT=0.795 min (H2O/MeOH with TFA, SunFire C18 2.5 μM, 2.1×30 mm, gradient=2 min, wavelength=220 nm); MS(ES): m/z=292 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 7.59 (dd, J=6.9, 2.3 Hz, 1H), 7.52-7.42 (m, 2H), 3.89 (s, 3H), 2.39 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. customto provide Intermediate A18A (11.51 g, 100%)

Sources & evidence

ORD record
ord-f84aee2a535f48ac81d9f7771d3757e0
Source dataset
uspto-grants-2016_01
Patent number
US09242941B2

Reaction notes

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