2-Methoxyaniline → HCID 19029312, compound

HRID 2256309Notes

Reaction equation

HRID 2256309 reaction equation
[Cl: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[Cl:8].[CH3:17][O:18][C:19]1[C:20]([NH2:25])=[CH:21][CH:22]=[CH:23][CH:24]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:10][C:11]([NH:25][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[O:18][CH3:17])=[O:12])[CH2:15][C:14]([OH:13])=[O:16])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 70002-MethoxyanilineHCID 8471TriethylamineHCID 543639424-(3,4-Dichlorophenyl)oxane-2,6-dione

Product 1

HCID 19029312HCID 19029312, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

3-(3,4-Dichlorophenyl)glutaric anhydride (10 g, Example 1, Step C) in CH2Cl2 (150 mL) at 0° C. was treated sequentially with o-anisidine (6 mL), triethylamine (6.7 mL) and N,N-dimethylaminopyridine (440 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 (500 mL) and washed with 1N HCl (1×200 mL) and water (1×200 mL). The organic layers were dried over MgSO4, filtered and concentrated to afford the title compound (14 g).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 12 hours
  3. washwashed with 1N HCl (1×200 mL) and water (1×200 mL)
  4. dry with materialThe organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bb153de115a84d40b8d456922e79f6d6
Source dataset
uspto-grants-1997_08
Patent number
US05654316

Reaction notes

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