Hydrochloric Acid → HCID 178479096, compound

HRID 1838843Notes

Reaction equation

HRID 1838843 reaction equation
[OH-].[NH4+].[N+:3]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([C:17]([F:20])([F:19])[F:18])[CH:10]=2)([O-])=O.[ClH:21]>[Pd].CO.C(OCC)C>[ClH:21].[NH2:3][C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([C:17]([F:20])([F:18])[F:19])[CH:10]=2

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 178526771HCID 178526771, compound

Product 1

HCID 178479096HCID 178479096, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A Parr flask was charged with methanol (40 mL), ammonium hydroxide (10 mL), 3-nitro-7-(trifluoromethyl)-4-quinolinol (12.8 g, 49.6 mmol) and palladium on carbon (1.0 g of 10%). The mixture was placed on a Parr apparatus under a hydrogen atmosphere at 40 psi (2.8 Kg/cm2) for 4 hours. The mixture was filtered and the catalyst was washed with methanol and dichloromethane. The combined organics were concentrated under vacuum to provide a green solid. The solid was dissolved in methanol and then combined with 1 N hydrochloric acid in anhydrous diethyl ether (150 mL). A precipitate formed almost immediately. The reaction mixture was allowed to stir for 16 hours. The precipitate was isolated by filtration, washed with diethyl ether and then dried in a vacuum oven at 80° C. to provide 9.3 g of 3-amino-7-(trifluoromethyl)-4-quinolinol hydrochloride as an off-white solid.

Workup

  1. filtrationThe mixture was filtered
  2. washthe catalyst was washed with methanol and dichloromethane
  3. concentrationThe combined organics were concentrated under vacuum
  4. customto provide a green solid
  5. customA precipitate formed almost immediately
  6. customThe precipitate was isolated by filtration
  7. washwashed with diethyl ether
  8. customdried in a vacuum oven at 80° C.

Sources & evidence

ORD record
ord-db7197c6c14d437e9dea54aac6868d44
Source dataset
uspto-grants-2004_01
Patent number
US06677334B2

Reaction notes

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