Hydrochloric Acid → HCID 23505674, compound

HRID 991538Notes

Reaction equation

HRID 991538 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([C:10]3[C:19]4[C:14](=[CH:15][C:16]5[O:22][CH2:21][O:20][C:17]=5[CH:18]=4)[C:13](=[O:23])[NH:12][N:11]=3)=[CH:4][C:3]=2[O:2]1.Br.Br[CH2:26][CH2:27][N:28]1[CH:32]=[CH:31][N:30]=[CH:29]1.C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C.CCOC(C)=O>[N:28]1([CH2:27][CH2:26][N:12]2[N:11]=[C:10]([C:5]3[CH:6]=[CH:7][C:8]4[O:9][CH2:1][O:2][C:3]=4[CH:4]=3)[C:19]3[C:14](=[CH:15][C:16]4[O:22][CH2:21][O:20][C:17]=4[CH:18]=3)[C:13]2=[O:23])[CH:32]=[CH:31][N:30]=[CH:29]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 23505599HCID 23505599, compoundHCID 509985161-(2-Bromoethyl)-1H-imidazole hydrobromide

Product 1

HCID 23505674HCID 23505674, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-(3,4-methylenedioxyphenyl)-6,7-methylenedioxy-1(2H)-phthalazinone (133 mg, 0.43 mmol), 1-(2-bromoethyl)imidazole hydrogen bromide (439 mg, 1.72 mmol), and K2CO3 (415 mg, 3.0 mmol) in DMF (10 mL) was stirred for 5 h at 70° C. The mixture was cooled, and 2N HCl and EtOAc were added to the mixture. The acidic aqueous layer was separated, made alkaline with 5% K2CO3 solution, and extracted with EtOAc. The extract was washed with brine, dried and concentrated under reduced pressure. The residual solid were purified by chromatography, on silica gel with CHCl3-MeOH (20:1) to afford the product as a white solid (27 mg, 16%). 300 MHz 1H-NMR (CDCl3): δ 7.78 (s, 1H), 7.37 (s, 1H), 7.04-6.86 (m, 5H), 6.13 (s, 2H), 6.03 (s, 2H), 4.58 (m, 2H), 4.45 (m, 2H).

Workup

  1. temperatureThe mixture was cooled
  2. customThe acidic aqueous layer was separated
  3. extractionextracted with EtOAc
  4. washThe extract was washed with brine
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residual solid were purified by chromatography, on silica gel with CHCl3-MeOH (20:1)

Sources & evidence

ORD record
ord-b4a90e53add446409db054dc35fe4357
Source dataset
uspto-grants-2002_10
Patent number
US06465472B1

Reaction notes

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