N-Methylaniline → HCID 70196436, compound

HRID 2256289Notes

Reaction equation

HRID 2256289 reaction equation
[C:1]1([CH:7]2[CH2:13][C:12](=[O:14])[O:11][C:9](=[O:10])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH2:23]([N:25](CC)CC)C>C(Cl)Cl>[C:17]1([CH2:23][NH:25][C:12](=[O:14])[CH2:13][CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][C:9]([OH:11])=[O:10])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 7515N-MethylanilineHCID 8471TriethylamineHCID 2978824-Phenyloxane-2,6-dione

Product 1

HCID 70196436HCID 70196436, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-Phenylglutaric anhydride (8.0 g) in CH2Cl2 (100 mL) at 0° C. was treated sequentially with N-methylaniline (5.63 g), triethylamine (5.32 g) and N,N-dimethylaminopyridine (1.0 g). 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 washed with 1N HCl (2×50 mL) and water (100 mL). The organic layers were dried over MgSO4, filtered and concentrated to afford the title compound (11.5 g).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 12 hours
  3. washThe reaction mixture was washed with 1N HCl (2×50 mL) and water (100 mL)
  4. dry with materialThe organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e0dc129092434f698273c319315df8be
Source dataset
uspto-grants-1997_08
Patent number
US05654316

Reaction notes

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