Hydrochloric Acid → HCID 9993627, compound

HRID 1061846Notes

Reaction equation

HRID 1061846 reaction equation
CO[C:3]1[CH:8]=[CH:7][C:6]([O:9]C)=[CH:5][C:4]=1[NH:11][C:12]([C:14]1[C:23]2[C:18](=[CH:19][C:20]([OH:24])=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)=[O:13].Cl.N1C=CC=CC=1.Cl>>[OH:24][C:20]1[CH:19]=[C:18]2[C:23](=[CH:22][CH:21]=1)[C:14]([C:12]1[O:13][C:3]3[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][C:4]=3[N:11]=1)=[CH:15][CH:16]=[CH:17]2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 10176127Pyridinium chlorideHCID 22285700N-(2,5-Dimethoxyphenyl)-6-hydroxynaphthalene-1-carboxamide

Product 1

HCID 9993627HCID 9993627, compoundYield 85%

Conditions

Temperature
200 °C

Procedure

A mixture of N-(2,5-dimethoxyphenyl)-6-hydroxy-1-naphthamide (2.0 g, 6.2 mmol), and pyridine hydrochloride (4.0 g, 34.6 mmol) was heated at 200° C. for 1 h. The reaction mixture was cooled to room temperature, acidified with HCl (2N) and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography (hexanes/EtOAc 1/1) gave a tan solid (1.45 g, 85% yield, m.p. 232-234° C.); MS m/e 278 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with EtOAc
  3. dry with materialThe organic extracts were dried over MgSO4
  4. customEvaporation and purification by flash chromatography (hexanes/EtOAc 1/1)

Sources & evidence

ORD record
ord-3a9c37bad11a459ea4633126ed94a204
Source dataset
uspto-grants-2005_11
Patent number
US06960607B2

Reaction notes

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