Trifluoroacetic acid → HCID 22226555, compound

HRID 1519746Notes

Reaction equation

HRID 1519746 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][C:12]([O:14]C(C)(C)C)=[O:13])=[CH:3][N:2]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][C:12]([OH:14])=[O:13])=[CH:3][N:2]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68755446HCID 68755446, compound

Product 1

HCID 22226555HCID 22226555, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(isoquinolin-4-yl)acetate (1.8 g, 7.4 mmol) in DCM (10 mL) was added TFA (10 mL) dropwise. The reaction was stirred at room temperature overnight. After the reaction completed, the solvent was evaporated and the residue was neutralized with aqueous ammonia to pH 3-4, then the precipitate was filtered, washed with water and ether, and the ether extract was collected to give the title compound (1.3 g, 93%) LC-MS (0.05% TFA): [M+1]+ 188.1. 1H-NMR (DMSO-d6, 400MHz): δ9.39 (s, 1H), 8.48 (s, 1H), 8.24 (d, 1H, J=6.4 Hz), 7.93 (t, 1H), 7.79 (m, 1H), 4.11 (s, 2H).

Workup

  1. customthe solvent was evaporated
  2. filtrationthe precipitate was filtered
  3. washwashed with water and ether
  4. extractionthe ether extract
  5. customwas collected

Sources & evidence

ORD record
ord-6946012aba964ead9604595a264cfdb5
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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