4-Chloroaniline → HCID 69200733, compound

HRID 2115776Notes

Reaction equation

HRID 2115776 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([OH:14])=O)=[CH:7][CH:6]=[CH:5]2.CCN(C(C)C)C(C)C.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=1>O=S(Cl)Cl.CN(C=O)C.CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:12]([C:8]2[C:9]3[C:4](=[CH:3][C:2]([OH:1])=[CH:11][CH:10]=3)[CH:5]=[CH:6][CH:7]=2)=[O:14])=[CH:27][CH:26]=1

Participants

8

Reactant 3

HCID 78124-ChloroanilineHCID 81531DiisopropylethylamineHCID 54638006-Hydroxy-1-naphthoic acid

Product 1

HCID 69200733HCID 69200733, compound

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A slurry of 6-hydroxy-naphthalene-1-carboxylic acid (0.2 g, 1.06 mmol) in 10.6 mL of SOCl2 and 1 drop of DMF was heated to 40° C. After 4 h, the solution was concentrated to dryness and placed under high vacuum overnight. The crude residue was dissolved in 3.5 mL of CH2Cl2. To the resulting solution was added DIEA (0.554 mL, 3.18 mmol), 4-chlorophenylamine (0.162 g, 1.27 mmol) and a catalytic amount of DMAP. The reaction was stirred under an argon atmosphere for 2 days. The reaction was diluted with CH2Cl2, washed with saturated aqueous NH4Cl, saturated aqueous NaHCO3, and brine. The organic layer was dried (Na2SO4), filtered and concentrated. The residue was passed through a medium-pressure silica gel column (solvent gradient: 94:6 CH2Cl2:MeOH; 95:5 CH2Cl2:MeOH; 90:10 CH2Cl2:MeOH) to afford the desired crude compound. The fractions were concentrated to dryness to afford a solid residue. The residue was triturated with CHCl3 to afford the desired compound as a pale yellow solid.

Workup

  1. concentrationthe solution was concentrated to dryness
  2. customplaced under high vacuum overnight
  3. dissolutionThe crude residue was dissolved in 3.5 mL of CH2Cl2
  4. washwashed with saturated aqueous NH4Cl, saturated aqueous NaHCO3, and brine
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c362dad7e00b4456a7052cea8d206dc4
Source dataset
uspto-grants-2008_10
Patent number
US07435823B2

Reaction notes

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