Sodium Carbonate → HCID 59382310, compound

HRID 2412170Notes

Reaction equation

HRID 2412170 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.Br[CH2:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[C:16]([Cl:21])=[CH:15][C:14]=1[CH2:22]Br.C([O-])([O-])=O.[Na+].[Na+]>CC(C)=O.CC(C)=O.O>[Cl:21][C:16]1[CH:15]=[C:14]2[C:13](=[CH:18][C:17]=1[O:19][CH3:20])[CH2:12][N:8]([CH2:7][C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH2:22]2

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 754524-MethoxybenzylamineHCID 59382304HCID 59382304, compound

Product 1

HCID 59382310HCID 59382310, compoundYield 14.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

A solution of 4-methoxybenzylamine (2.4 g, 17.6 mmol) in acetone (110 ml) was added dropwise to a mixture of 1,2-bis-bromomethyl-4-chloro-5-methoxy-benzene (assumed theoretical, 17.6 mmol) and Na2CO3 (12 g, 114 mmol) in acetone/water (10 ml:12.5 ml) then stirred at room temperature for 2 hours and concentrated in vacuo. The crude material was dissolved in ethyl acetate and extracted with 2N HCl. The aqueous layer was neutralized with sodium carbonate, extracted with ethyl acetate (×2), dried (MgSO4) and evaporated under vacuum to give 5-chloro-6-methoxy-2-(4-methoxy-benzyl)-2,3-dihydro-1H-isoindole (0.8 g, 2.6 mmol) as a brown gum. MS: [M+H]+ 304

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe crude material was dissolved in ethyl acetate
  3. extractionextracted with 2N HCl
  4. extractionextracted with ethyl acetate (×2)
  5. dry with materialdried (MgSO4)
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-d89266f351a549e9baea9fcd7b77d1dc
Source dataset
uspto-grants-2014_08
Patent number
US08816087B2

Reaction notes

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