Hydrochloric Acid → HCID 18386558, compound

HRID 380945Notes

Reaction equation

HRID 380945 reaction equation
CC(C)(C)C([NH:5][C:6]1[C:11]([F:12])=[CH:10][C:9]([Cl:13])=[CH:8][C:7]=1[C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])=O.Cl.C([O-])([O-])=O.[K+].[K+]>COCCOC>[NH2:5][C:6]1[C:11]([F:12])=[CH:10][C:9]([Cl:13])=[CH:8][C:7]=1[C:14](=[O:19])[C:15]([F:18])([F:17])[F:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 53650418HCID 53650418, compound

Product 1

HCID 18386558HCID 18386558, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A stirred solution of 0.35 g (1.07 mmol) of 2′-(trimethylacetamido)-5′-chloro-3′-fluoro-2,2,2-trifluoroacetophenone in 3 mL of 1,2-dimethoxyethane and treated with 24 mL of 6N aq. HCl. The mixture was stirred at reflux for 2 h, cooled to RT, and brought to pH 9 with K2CO3. The mixture was extracted twice with ether and the combined organic extracts were washed with brine, dried (MgSO4), and concentrated under reduced pressure to give 240 mg (92%) of 2′-amino-5′-chloro-3′-fluoro-2,2,2-trifluoroacetophenone as an oily orange solid. 1H NMR (300 MHz CDCl3) δ 7.54(m, 1H); 7.25(dd, 1H, J=10.6, 2.2 Hz); 6.40-6.60(br. s, 2H). High resolution mass spec: calculated for C8H4NOClF4(M+): 240.9918, found: 240.9914. 19F NMR (282 MHz, CDCl3) δ −132.7(s, 1F), −70.6(s, 3F).

Workup

  1. temperatureat reflux for 2 h
  2. extractionThe mixture was extracted twice with ether
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3dc8231efd20445c8741180f28c4f94e
Source dataset
uspto-grants-2001_10
Patent number
US06303780B1

Reaction notes

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