Chloride → N-(6-Hydroxy-naphthalen-1-yl)-benzamide

HRID 1925274Notes

Reaction equation

HRID 1925274 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([OH:12])=[CH:7]2.[C:13]([O-:16])([O-])=O.[K+].[K+].[Cl-].O>C(Cl)Cl>[OH:12][C:6]1[CH:7]=[C:8]2[C:3](=[CH:4][CH:5]=1)[C:2]([NH:1][C:13](=[O:16])[C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:3]=1)=[CH:11][CH:10]=[CH:9]2

Participants

6

Reactant 4

HCID 312ChlorideHCID 962WaterHCID 68655-Amino-2-naphtholHCID 11430Potassium Carbonate

Product 1

HCID 67520279N-(6-Hydroxy-naphthalen-1-yl)-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a round bottom flask containing 1.00 g (6.3 mmol) 5-amino-naphthalene-2-ol in 10 mL CH2Cl2, was added 2.61 g (0.0189 mmol) K2CO3, followed by 1.46 mL (0.0126 mmol) benzolyl chloride. The solution mixture was stirred under inert atmosphere until completion. After stirring for 18 h, water was added into the mixture and diluted with CH2Cl2. The organics were separated by sep. funnel, while extracting the organics 3× with CH2Cl2. The organic layers were combined, dried over Na2SO4, filtered and concentrated in-vacuo. The crude was purified by crystallization in CH2Cl2/Hexanes. A gray colored powder was collected, which was titled compound. MS (ESI pos. ion) m/z: 264 (M+H)

Workup

  1. stirringAfter stirring for 18 h
  2. customThe organics were separated by sep
  3. extractionfunnel, while extracting the organics 3× with CH2Cl2
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in-vacuo
  7. customThe crude was purified by crystallization in CH2Cl2/Hexanes
  8. customA gray colored powder was collected

Sources & evidence

ORD record
ord-8ff2bdf2772242e1b5a5d789e259eb82
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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