3-Chloroaniline → HCID 11454551, compound

HRID 1925284Notes

Reaction equation

HRID 1925284 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[CH:25]=[C:24]2[C:19]([CH:20]=[CH:21][C:22]([C:26]([OH:28])=O)=[CH:23]2)=[CH:18][CH:17]=1.CCN(C(C)C)C(C)C.[Cl:38][C:39]1[CH:40]=[C:41]([CH:43]=[CH:44][CH:45]=1)[NH2:42]>CN(C=O)C.C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[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[CH:25]=[C:24]2[C:19]([CH:20]=[CH:21][C:22]([C:26]([NH:42][C:41]3[CH:43]=[CH:44][CH:45]=[C:39]([Cl:38])[CH:40]=3)=[O:28])=[CH:23]2)=[CH:18][CH:17]=1

Participants

8

Reactant 3

HCID 79323-ChloroanilineHCID 81531DiisopropylethylamineHCID 67520412HCID 67520412, compound

Product 1

HCID 11454551HCID 11454551, compound

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A slurry of 7-(6,7-dimethoxyquinolin-4-yloxy)-2-naphthoic acid (0.54 g, 1.44 mmol) in 10 mL of C2O2Cl2 and 2 drops of DMF was stirred at RT. After 2 h, the solution was concentrated to dryness and placed under high vacuum overnight. A portion of the crude residue (0.075 g, 0.191 mmol) was dissolved in 1 mL of CH2Cl2. To the resulting solution was added DIPEA (0.133 mL, 0.764 mmol), 3-chloroaniline (0.024 mL, 0.229 mmol) and a catalytic amount of DMAP. The reaction was stirred under a N2 atmosphere for 16 h. The reaction was diluted with EtOAc, and washed with saturated aqueous NaHCO3. The organic layer was dried (MgSO4), filtered and concentrated. The residue was passed through a medium-pressure silica gel column (solvent gradient: 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 Et2O/Hexanes to afford the desired compound as a pale yellow solid. MS (ESI, pos. ion) m/z: 485.0 (M+1). Mass Calc'd for C28H21ClN2O4: 484.937.

Workup

  1. concentrationthe solution was concentrated to dryness
  2. customplaced under high vacuum overnight
  3. washwashed with saturated aqueous NaHCO3
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c6a0d43f3be548be843082cae286f1ac
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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