Ammonia → 2-(Isoquinolin-8-YL)acetic acid

HRID 1519749Notes

Reaction equation

HRID 1519749 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:11][C:12]([O:14]C(C)(C)C)=[O:13])[CH:4]=[CH:3][N:2]=1.C(O)(C(F)(F)F)=O.N>C(Cl)Cl>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:11][C:12]([OH:14])=[O:13])[CH:4]=[CH:3][N:2]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 68757728Tert-butyl 2-(isoquinolin-8-yl)acetate

Product 1

HCID 179072422-(Isoquinolin-8-YL)acetic acidYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(isoquinolin-8-yl)acetate (1.8 g) in DCM (10 mL) was added TFA (10 mL) dropwise. The reaction was stirred at room temperature overnight. After the reaction was complete, the solvent was removed to give a residue which was adjusted to pH 3-4 with aqueous ammonia. The precipitate was filtered off and washed with water. The final product was purified (silica gel coulumn chromatography) to afford 2-(isoquinolin-8-yl)acetic acid as a solid (1.2 g, 87%). LC-MS (0.05% TFA): [M+1]+ 188.1. 1H-NMR (DMSO-d6, 400MHz): δ13.0 (brs, 1H), 9.65(s, 1H), 8.61(d, 1H, J=4.8Hz), 8.16 (d, 1H, J=4.8Hz), 8.05 (d, 1H, J=6.8Hz), 7.92 (t, 1H), 7.72 (d, 1H, J=6.8Hz), 4.29 (s, 2H).

Workup

  1. customthe solvent was removed
  2. customto give a residue which
  3. filtrationThe precipitate was filtered off
  4. washwashed with water
  5. customThe final product was purified (silica gel coulumn chromatography)

Sources & evidence

ORD record
ord-25383730900d4abb859982aee86cf16e
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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