HCID 18421399, compound → HCID 18421446, compound

HRID 368787Notes

Reaction equation

HRID 368787 reaction equation
[C:1]([O:4][C:5]1[C:14]([CH3:15])=[C:13]2[C:8]([C:9]([CH3:19])=[C:10]([CH2:17]Br)[C:11](=[O:16])[O:12]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[C:20]1(=[O:30])[NH:24][C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12.[K]>CN(C=O)C>[C:1]([O:4][C:5]1[C:14]([CH3:15])=[C:13]2[C:8]([C:9]([CH3:19])=[C:10]([CH2:17][N:24]3[C:23](=[O:25])[C:22]4=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]4[C:20]3=[O:30])[C:11](=[O:16])[O:12]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 18421399HCID 18421399, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 18421446HCID 18421446, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-acetoxy-3-bromomethyl-4,8-dimethylcoumarin (200 mg, 0.617 mmol) and potassium phthalimide (126 mg, 0.680 mmol) was stirred overnight at room temperature in DMF (3 mL). The slurry was poured into ice water, filtered and washed with a copious amount of water to remove traces of DMF to give 7-acetoxy-4,8-dimethyl-3-phthalimidomethylcoumarin, a creamy white solid after drying (221 mg, 91.7%). 1H NMR (CDCl3): δ 7.84-7.67 (m, 4H), 7.55 (d, J=8.8 Hz, 1H), 7.02 (d, J=8.8 Hz, 1H), 4.92 (s, 2H), 2.62 (s, 3H), 2.36 (s, 3H), 2.25 (s, 3H).

Workup

  1. filtrationfiltered
  2. washwashed with a copious amount of water
  3. customto remove traces of DMF

Sources & evidence

ORD record
ord-fb77841d793d41e58c351ad23d158fc8
Source dataset
uspto-grants-2000_10
Patent number
US06133460

Reaction notes

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