Hydrochloric Acid → 4-(3-Cyano-5,6-difluoroindol-1-yl)-2-hydroxybenzoic acid ethyl ester

HRID 73352Notes

Reaction equation

HRID 73352 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([F:21])=[C:17]([F:20])[CH:18]=3)[C:13]([C:22]#[N:23])=[CH:12]2)=[CH:7][C:6]=1[O:24]COC)[CH3:2].O1CCCC1.Cl>C(O)C>[CH2:1]([O:3][C:4](=[O:28])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([F:21])=[C:17]([F:20])[CH:18]=3)[C:13]([C:22]#[N:23])=[CH:12]2)=[CH:7][C:6]=1[OH:24])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 58437363HCID 58437363, compound

Product 1

HCID 584372264-(3-Cyano-5,6-difluoroindol-1-yl)-2-hydroxybenzoic acid ethyl esterYield 69.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-(3-cyano-5,6-difluoroindol-1-yl)-2-methoxymethoxybenzoic acid ethyl ester (0.12 g) in a mixed solvent of tetrahydrofuran (1.5 mL) and ethanol (3 mL) was added 2 mol/L hydrochloric acid (1.0 mL), and this mixture was stirred at 70° C. overnight. After cooling to ambient temperature, the precipitated solid was collected by filtration, and washed with water and n-hexane, and dried under reduced pressure at 40° C. to give the title compound (0.074 g).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with water and n-hexane
  4. customdried under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-f4a967c532304d3c9aa27556cbb2bcc3
Source dataset
uspto-grants-2014_09
Patent number
US08829040B2

Reaction notes

Loading…