p-Anisoyl chloride → HCID 67387223, compound

HRID 908316Notes

Reaction equation

HRID 908316 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.[C:13](Cl)(=[O:22])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[OH:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([NH:1][C:13](=[O:22])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[CH:11]=[CH:10]2

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 11430Potassium CarbonateHCID 4286056-Amino-2-naphthalenol

Product 1

HCID 67387223HCID 67387223, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 100 mL round-bottomed flask containing 6-aminonaphthalen-2-ol (0.600 g, 3.8 mmol), in DCM (10 mL), was added p-Anisoyl chloride (0.972 g, 5.7 mmol), along with K2CO3 (1.57 g, 11.4 mmol). The mixture was stirred at ambient temperature overnight and was diluted with DCM and H2., Extraction with DCM (3×10 mL), drying of the organics over sodium sulfate, filtration, and concentration in-vacuo afforded the crude product. Recrystallization of the crude from DCM/Hexanes gave a tan colored amorphous solid, after drying (0.300 g, 1.0 mmol). MS (ESI pos. ion) m/z: 294 (M+H). Calc'd Exact Mass for C18H15NO3: 293.

Workup

  1. extraction, Extraction with DCM (3×10 mL)
  2. customdrying of the
  3. filtrationorganics over sodium sulfate, filtration, and concentration in-vacuo

Sources & evidence

ORD record
ord-beb7e1ed2df245efb9a7a8f2861768bc
Source dataset
uspto-grants-2011_09
Patent number
US08017601B2

Reaction notes

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