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Hydrochloric Acid → 2-(1H-Indazol-5-yloxy)-5-fluorobenzonitrile

HRID 220218
Notes
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Reaction equation

HRID 220218 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:13][C:14]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:15]=3[C:16]#[N:17])=[CH:10][CH:11]=2)[CH:6]=[N:5]1)(=O)C.Cl.[OH-].[Na+].O>CO>[NH:4]1[C:12]2[C:7](=[CH:8][C:9]([O:13][C:14]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:15]=3[C:16]#[N:17])=[CH:10][CH:11]=2)[CH:6]=[N:5]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 575522842-(1-acetyl-1H-indazol-5-yloxy)-5-fluorobenzonitrile

Product 1

HCID 574187532-(1H-Indazol-5-yloxy)-5-fluorobenzonitrileYield 91.2%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Conditions

Temperature
70 °C

Procedure

2-(1-Acetyl-1H-indazol-5-yloxy)-5-fluorobenzonitrile (369.4 mL, 221.7 mmol) in 370 mL MeOH was treated with 1.0 N HCl (243.8 mL, 243.8 mmol) at ambient temperature. The brown suspension was warmed to 70° C. for 28 hours and then cooled to 0° C. Sodium hydroxide (254.9 mL, 254.9 mmol) was added, followed by water (400 mL). The reaction was stirred at 0° C. for 15 minutes and then filtered. The solids were washed with water (1.5 and dried under high vacuum at 40° C. for 72 hours to provide 51.2 g of the desired product as a tan solid (91% yield for steps 2 and 3).

Workup

  1. temperaturecooled to 0° C
  2. filtrationfiltered
  3. washThe solids were washed with water (1.5
  4. customdried under high vacuum at 40° C. for 72 hours

Sources & evidence

ORD record
ord-fdfe3b45dcf14d04a9f954999320dbad
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08202899B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes