HCID 86647901, compound → HCID 68453416, compound

HRID 1969323Notes

Reaction equation

HRID 1969323 reaction equation
[ClH:1].[NH2:2][CH2:3]/[CH:4]=[C:5](/[F:18])\[CH2:6][O:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][CH:9]=1>Cl>[ClH:1].[NH3+:2][CH2:3]/[CH:4]=[C:5](/[F:18])\[CH2:6][O:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O-:14])=[O:13])=[CH:10][CH:9]=1

Participants

3

Reactant 1

HCID 86647901HCID 86647901, compound

Product 1

HCID 68453416HCID 68453416, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A stirred solution of (E)-Methyl 4-(4-amino-2-fluorobut-2-enyloxy)benzoate hydrochloride (0.050 g, 0.18 mmol) in ethereal HCl solution (1 M; 3 mL) was stirred at reflux for 20 hours. The reaction mixture was allowed to cool to RT and the volatiles were removed under reduced pressure to afford the title compound (0.040 g, 98%) as a fine white powder; m.p.=256-257° C.; 1H-NMR (200 MHz, D2O): δppm: 3.77 (2H, d, J 8.4 Hz), 4.91 (2H, d, J 18.8 Hz), 5.65 (1H, dt, J 18.6, 8.0 Hz), 7.08 (2H, d, J 8.4 Hz), 8.00 (2H, d, J 8.4 Hz).

Workup

  1. temperatureat reflux for 20 hours
  2. customthe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-6404108275d34d1ea9ee491cfbcbf8cf
Source dataset
uspto-grants-2013_04
Patent number
US08426587B2

Reaction notes

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