Ammonia → HCID 25059693, compound

HRID 2244073Notes

Reaction equation

HRID 2244073 reaction equation
[NH3:1].[C:2]([C:4]([C:9]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:10]=1[C:11]#[N:12])=[CH:5]OCC)#[N:3]>CO>[NH2:1][C:11]1[C:10]2[C:9](=[CH:16][C:15]([F:17])=[CH:14][CH:13]=2)[C:4]([C:2]#[N:3])=[CH:5][N:12]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 675306412-Cyano-α-(ethoxymethylene)-5-fluorobenzeneacetonitrile

Product 1

HCID 25059693HCID 25059693, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ammonia in MeOH (7 N, 20 mL) is added to 2-(1-cyano-2-ethoxy-vinyl)-4-fluoro-benzonitrile (0.88 g, 4 mmol). The reaction mixture is stirred at RT for 5 h. The orange precipitate is collected by vacuum filtration to afford 0.297 g (40%) of 1-amino-6-fluoro-isoquinoline-4-carbonitrile as an orange solid. LC/MS m/z=188 [M+H]+, RT=2.10-2.15 min. 1H NMR (CDCl3, 25 deg, 500 MHz): δ 8.44 (dd, 2H), 8.18 (t, 1H), 8.04 (bs, 4H), 7.73 (d, 1H), 7.63 (dt, 1H), 7.53 (dt, 2H), 7.43 (dd, 2H)

Workup

  1. filtrationThe orange precipitate is collected by vacuum filtration

Sources & evidence

ORD record
ord-cc7ca733b1dd409d81edab92c0c5d3d6
Source dataset
uspto-grants-2010_03
Patent number
US07678803B2

Reaction notes

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