Hydrochloric Acid → HCID 18451486, compound

HRID 1270758Notes

Reaction equation

HRID 1270758 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([NH:13][C:14](=[O:16])[CH3:15])=[CH:10]2)=[CH:5][CH:4]=1.[Cl:19]N1C(=O)CCC1=O.Cl>C(O)(=O)C>[Cl:19][C:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([C:2]([F:17])([F:18])[F:1])[CH:12]=2)[CH:7]=[CH:8][C:9]=1[NH:13][C:14](=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31398ChlorosuccinimideHCID 18451538N-[7-(Trifluoromethyl)-2-naphthalenyl]acetamide

Product 1

HCID 18451486HCID 18451486, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
50 °C

Procedure

A mixture of 7-trifluoromethyl-2-acetamidonaphthalene (620 mg, 2.45 mmol), N-chlorosuccinimide (326 mg, 2.45 mmol) and 1 M HCl in acetic acid (2.45 mL, 2.45 mmol) in acetic acid (10 mL) is heated at 50° C. under a N2 atmosphere for 1 hour. After cooling to room temperature, the mixture is partitioned between EtOAc and water. The organic layer is washed with brine, dried (Na2SO4) and concentrated by rotary evaporator to give 1-chloro-7-trifluoromethyl-2-acetamidonaphthalene as an off-white solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe mixture is partitioned between EtOAc and water
  3. washThe organic layer is washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated by rotary evaporator

Sources & evidence

ORD record
ord-34f63787d3f44d69bbf028e79cf80b27
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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