N-Methylaniline → HCID 70194865, compound

HRID 2256283Notes

Reaction equation

HRID 2256283 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:15][C:14](=[O:16])[O:13][C:11](=[O:12])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8].CN[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[CH2:25]([N:27](CC)CC)C>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:10][C:11]([NH:27][CH2:25][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:12])[CH2:15][C:14]([OH:13])=[O:16])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 7515N-MethylanilineHCID 8471TriethylamineHCID 11499576HCID 11499576, compound

Product 1

HCID 70194865HCID 70194865, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

3-(3,4-Difluorophenyl)glutaric anhydride (3.61 g) in CH2Cl2 (75 mL) at 0° C. was treated sequentially with N-methylaniline (2.16 mL), triethylamine (2.78 mL) and N,N-dimethylaminopyridine (195 mg). The mixture was stirred at 0° C. for two hours then allowed to warm to room temperature and stirred for 12 hours. The reaction mixture was diluted with CH2Cl2 (300 mL) and washed with 1N HCl (1×100 mL) and water (1×100 mL). The organic layers were dried over MgSO4, filtered and concentrated to afford the title compound (4.3 g).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 12 hours
  3. washwashed with 1N HCl (1×100 mL) and water (1×100 mL)
  4. dry with materialThe organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-01b94f0a0e5c4309a019ec8ffc5a55e8
Source dataset
uspto-grants-1997_08
Patent number
US05654316

Reaction notes

Loading…