Chloride → 6-(Isoquinolin-5-yl)naphthalene-1-carboxamide

HRID 908327Notes

Reaction equation

HRID 908327 reaction equation
[CH:1]1[C:10]2[C:5](=[C:6]([C:11]3[CH:12]=[C:13]4[C:18](=[CH:19][CH:20]=3)[C:17]([C:21](O)=[O:22])=[CH:16][CH:15]=[CH:14]4)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[Cl-].C[N:26](C=O)C>C(Cl)Cl>[CH:1]1[C:10]2[C:5](=[C:6]([C:11]3[CH:12]=[C:13]4[C:18](=[CH:19][CH:20]=3)[C:17]([C:21]([NH2:26])=[O:22])=[CH:16][CH:15]=[CH:14]4)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

5

Reactant 3

HCID 312ChlorideHCID 6228DimethylformamideHCID 58828852HCID 58828852, compound

Product 1

HCID 588288596-(Isoquinolin-5-yl)naphthalene-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-(isoquinolin-5-yl)-1-naphthoic acid (0.86 mg, 0.29 mmol) was suspended in CH2Cl2 (2 mL) and oxallyl chloride (0.038 mL, 0.4 mmol) was added followed by a drop of DMF. Mixture was stirred at room temperature for 3 h and solvent was evaporated and residue dried under vacuum. The crude acid chloride was dissolved in a solution of NH3 in dioxane and was stirred at room temperature. Solvent was evaporated, a solution of aqueous NaHCO3 was added and the mixture was extracted with CH2Cl2 and then with ethyl acetate. Residue was purified by prep plate (5% MeOH/CH2Cl2) to give the title compound as a solid. MS (ESI pos. ion) m/z: 299. (M+H). Calc'd Exact Mass for C20H14N2O: 298.

Workup

  1. customsolvent was evaporated
  2. customresidue dried under vacuum
  3. dissolutionThe crude acid chloride was dissolved in a solution of NH3 in dioxane
  4. stirringwas stirred at room temperature
  5. customSolvent was evaporated
  6. additiona solution of aqueous NaHCO3 was added
  7. extractionthe mixture was extracted with CH2Cl2
  8. customResidue was purified by prep plate (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-bcc1d8c98b9a4a029c322892a42e191b
Source dataset
uspto-grants-2011_09
Patent number
US08017601B2

Reaction notes

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