Trifluoroacetic acid → 4-Aminoisoquinoline-1-carbonitrile

HRID 2110443Notes

Reaction equation

HRID 2110443 reaction equation
COC1C=C(OC)C=CC=1C[NH:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]#[N:18])=[N:9][CH:8]=1.FC(F)(F)C(O)=O>>[NH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]#[N:18])=[N:9][CH:8]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 218754144-(2,4-Dimethoxy-benzylamino)-isoquinoline-1-carbonitrile

Product 1

HCID 218752724-Aminoisoquinoline-1-carbonitrileYield 92%

Procedure

Compound 470C (50 mg, 0.16 mmol) was treated with trifluoroacetic acid (0.5 mL) for 1 h. The highly colored mixture was partitioned between ethyl acetate (30 mL) and 1N NaOH (30 mL). After washing with brine (15 mL), the organic layer was dried over magnesium sulfate and concentrated in vacuo to afford 24 mg (92%) of compound 470D as a yellow solid. HPLC: 99% at 1.09 min (retention time) (Phenomenex C-18, 5 micron column, 4.6×30 mm, eluting with 10-90% aqueous methanol over 2 min containing 0.1% TFA, 4 mL/min, monitoring at 254 nm). MS (ES+): m/z 170.2 [M+H]+.

Workup

  1. customThe highly colored mixture was partitioned between ethyl acetate (30 mL) and 1N NaOH (30 mL)
  2. washAfter washing with brine (15 mL)
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2596a63c23a84c839ddb3d6a0833cdd0
Source dataset
uspto-grants-2009_04
Patent number
US07517904B2

Reaction notes

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