Dichlone → HCID 22988629, compound

HRID 987201Notes

Reaction equation

HRID 987201 reaction equation
Cl[C:2]1[C:3](=[O:14])[C:4]2[C:9]([C:10](=[O:13])[C:11]=1Cl)=[CH:8][CH:7]=[CH:6][CH:5]=2.[NH2:15][C:16]1[CH:25]=[C:24]2[C:19]([C:20]([CH3:27])=[CH:21][C:22](=[O:26])[O:23]2)=[CH:18][CH:17]=1.[CH2:28]([N:30](CC)[CH2:31][CH3:32])[CH3:29].N1CCCC1>CN(C=O)C>[N:30]1([C:11]2[C:10](=[O:13])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3](=[O:14])[C:2]=2[NH:15][C:16]2[CH:25]=[C:24]3[C:19]([C:20]([CH3:27])=[CH:21][C:22](=[O:26])[O:23]3)=[CH:18][CH:17]=2)[CH2:31][CH2:32][CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 8342DichloneHCID 8471TriethylamineHCID 31268PyrrolidineHCID 922497-Amino-4-methylcoumarin

Product 1

HCID 22988629HCID 22988629, compoundYield 13.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2,3-dichloro-1,4-naphthoquinone (0.5 mmol, 114 mg) was dissolved in anhydrous DMF (1.5 mL) in a 5 mL vial. 7-Amino-4-methylcoumarin (0.5 mmol 88 mg) and triethylamine (0.5 mmol, 70 μL) were added. The solution was heated at 100°C. for 16 hr. Pyrrolidine (2 mmol, 0.17 mL) was added. The solution was heated at 100° C. for 16 hr. The excess volatile amines were removed under vacuum. The residue was dissolved in 3 mL acetonitrile containing 1% TFA. The crude product (1.0 mL) was purified with HPLC to give a dark purple solid (26.3 mg). 1H NMR (CDCl3): 8.09-7.98 (m, 2H), 7.64-7.55 (m, 2H), 7.45 (d, 1H, J=8.6 Hz), 6.74 (d, 1H, J=8.6 Hz), 6.31 (s, 1H), 6.09 (s, 1H), 3.63-3.54 (m, 4H), 2.36 (s, 3H), 1.78-1.69 (m, 4H) ppm.

Workup

  1. temperatureThe solution was heated at 100° C. for 16 hr
  2. customThe excess volatile amines were removed under vacuum
  3. dissolutionThe residue was dissolved in 3 mL acetonitrile containing 1% TFA
  4. customThe crude product (1.0 mL) was purified with HPLC

Sources & evidence

ORD record
ord-6d4bec09599e45b4827138ddbbe5d742
Source dataset
uspto-grants-2003_10
Patent number
US06630589B1

Reaction notes

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