Potassium Carbonate → HCID 70024652, compound

HRID 1358467Notes

Reaction equation

HRID 1358467 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([N+:19]([O-:21])=[O:20])=[C:13]([OH:18])[CH:14]=2)[CH:9]1[CH2:22][C:23]1[CH:28]=[C:27]([Br:29])[C:26]([O:30][CH3:31])=[C:25]([Br:32])[CH:24]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH3:39][O:40][C:41]1[CH:48]=[CH:47][C:44]([CH2:45]Cl)=[CH:43][CH:42]=1>CN(C=O)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([N+:19]([O-:21])=[O:20])=[C:13]([O:18][CH2:45][C:44]3[CH:47]=[CH:48][C:41]([O:40][CH3:39])=[CH:42][CH:43]=3)[CH:14]=2)[CH:9]1[CH2:22][C:23]1[CH:24]=[C:25]([Br:32])[C:26]([O:30][CH3:31])=[C:27]([Br:29])[CH:28]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chloride2×HCID 70024909HCID 70024909, compound

Product 1

HCID 70024652HCID 70024652, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(3,5-dibromo-4-methoxy-benzyl)-6-hydroxy-7-nitro-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid tert-butyl ester (0.002 mol), K2CO3 (0.331 g, 0.0024 mol) and 4-methoxybenzyl chloride (0.376 g, 0.0024 mol) in 10 mL of DMF was heated for 4 h at 100° C. 0.17 g (0.00109 mol) of 4-methoxybenzyl chloride was added additionally. The reaction mixture was heated for 5 h at 100° C., cooled, poured in water, cooled, filtered and dried in vacuum. The residue was dissolved in ethyl acetate and filtered through silica gel. The solution was concentrated. The residue was crystallized from chloroform-hexanes mixture. Yield 0.96 g (72%).

Workup

  1. temperatureThe reaction mixture was heated for 5 h at 100° C.
  2. temperaturecooled
  3. temperaturecooled
  4. filtrationfiltered
  5. customdried in vacuum
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. filtrationfiltered through silica gel
  8. concentrationThe solution was concentrated
  9. customThe residue was crystallized from chloroform-hexanes mixture

Sources & evidence

ORD record
ord-b53db483eedb469ca26b21cb3706c99c
Source dataset
uspto-grants-2003_07
Patent number
US06596734B1

Reaction notes

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