Hydrochloric Acid → HCID 14499221, compound

HRID 1165501Notes

Reaction equation

HRID 1165501 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[CH:7]=[CH:6]2.N1C=CC=CC=1.[C:27](Cl)(=[O:29])[CH3:28].Cl>C(Cl)Cl>[OH:20][C:17]1[CH:18]=[CH:19][C:14]([N:13]([C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:9]=2)[C:27](=[O:29])[CH3:28])=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6367Acetyl chlorideHCID 14499207HCID 14499207, compound

Product 1

HCID 14499221HCID 14499221, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 190 mg (0.72 mmol) of 4-[(6-methoxy-2-naphthyl)amino]phenol (prepared as described in Example 2) and 0.50 ml of pyridine (dried over KOH) in 4 ml of dry CH2Cl2 at 0° was added dropwise over 5 minutes 55 ul (0.77 mmol) of acetyl chloride. The reaction mixture was stirred for 30 minutes then added to 25 ml of 1N aqueous HCl solution and extracted with 25 ml of warm ethyl acetate. The organic extract was washed with an additional 25 ml of 1M aqueous HCl solution, dried (MgSO4) and concentrated in vacuo to give a solid. The crude solid was purified by flash chromatography (silica gel, 10×3.0 cm, 1:1 EtOAc/petroleum ether) followed by recrystallization (EtOAc/petroleum ether) to afford 145 mg (66%) of title compound as white crystals, m.p. 187°-188°.

Workup

  1. extractionextracted with 25 ml of warm ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with an additional 25 ml of 1M aqueous HCl solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give a solid
  7. customThe crude solid was purified by flash chromatography (silica gel, 10×3.0 cm, 1:1 EtOAc/petroleum ether)
  8. customfollowed by recrystallization (EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-6c84439077204948b50912fb448c8387
Source dataset
uspto-grants-1990_03
Patent number
US04910208

Reaction notes

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