4-Chloroaniline → HCID 67386813, compound

HRID 908326Notes

Reaction equation

HRID 908326 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](Cl)=[O:22])=[CH:16][CH:15]=[CH:14]4)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.C(N(CC)CC)C.[Cl:31][C:32]1[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C=O)C>[Cl:31][C:32]1[CH:38]=[CH:37][C:35]([NH:36][C:21]([C:17]2[C:18]3[C:19](=[CH:20][C:11]([C:6]4[CH:7]=[CH:8][CH:9]=[C:10]5[C:5]=4[CH:4]=[CH:3][N:2]=[CH:1]5)=[CH:12][CH:13]=3)[CH:14]=[CH:15][CH:16]=2)=[O:22])=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 78124-ChloroanilineHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 86611256HCID 86611256, compound

Product 1

HCID 67386813HCID 67386813, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

6-(isoquinolin-5-yl)-1-naphthoyl chloride (0.85 g, 0.27 mmol) was suspended in CH2Cl2 (1 mL) and triethylamine (0.057 mL, 0.4 mmol) was added followed by 4-chloroaniline (33 mg, 0.26 mol). The mixture was stirred at room temperature for 2 h, 0.1 mL of DMF was added and the mixture was stirred for an additional 72 h. A solution of aqueous NaHCO3 was added and mixture was extracted with CH2Cl2. Organic phase was dried, filtered and evaporated. Residue was purified by prep plate (ethyl acetate) to give a white solid. MS (ESI pos. ion) m/z: 409 (M+H). Calc'd Exact Mass for C26H17ClN2O: 408.

Workup

  1. stirringthe mixture was stirred for an additional 72 h
  2. extractionmixture was extracted with CH2Cl2
  3. customOrganic phase was dried
  4. filtrationfiltered
  5. customevaporated
  6. customResidue was purified by prep plate (ethyl acetate)
  7. customto give a white solid

Sources & evidence

ORD record
ord-7fffaada92564f8cb498ed682e93882d
Source dataset
uspto-grants-2011_09
Patent number
US08017601B2

Reaction notes

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