Benzoyl chloride → HCID 58732908, compound

HRID 1925256Notes

Reaction equation

HRID 1925256 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[C:17]([CH3:27])=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH:22]=[C:21]([NH2:26])[CH:20]=[CH:19]2.[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[C:17]([CH3:27])=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH:22]=[C:21]([NH:26][C:28](=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH:20]=[CH:19]2

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 11430Potassium CarbonateHCID 67520335HCID 67520335, compound

Product 1

HCID 58732908HCID 58732908, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-(6,7-Dimethoxy-quinolin-4-yloxy)-5-methyl-naphthalen-2-ylamine (Step b, 0.100 g, 0.2 mmol), benzoyl chloride (0.04 mL, 0.3 mmol) and K2CO3 (0.116 g, 0.6 mmol) in CH2Cl2 were stirred overnight under inert atmosphere. The reaction was quenched with water and diluted with CH2Cl2. The aqueous layer was extracted 3 times with CH2Cl2. The organics were collected, dried over Na2SO4, filtered, and concentrated in vacuo. The crude was purified by silica-gel column chromatography in EtOAc/Hexanes to give the titled compound as a rust colored film. MS (ESI, pos. ion) m/z: 465 (M+1). Mass Calc'd for C29H24N2O4: 464.17.

Workup

  1. customThe reaction was quenched with water
  2. additiondiluted with CH2Cl2
  3. extractionThe aqueous layer was extracted 3 times with CH2Cl2
  4. customThe organics were collected
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude was purified by silica-gel column chromatography in EtOAc/Hexanes

Sources & evidence

ORD record
ord-335f94746e5a463a88eb4f664f875881
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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