Sodium Carbonate → HCID 68536089, compound

HRID 1991073Notes

Reaction equation

HRID 1991073 reaction equation
[CH3:1][O:2][C:3](=[O:21])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][O:15][CH3:16])[C:9]([Cl:17])=[CH:8][C:7]=1[N+:18]([O-])=O.Cl[Sn]Cl.C([O-])([O-])=O.[Na+].[Na+]>CO>[CH3:1][O:2][C:3](=[O:21])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][O:15][CH3:16])[C:9]([Cl:17])=[CH:8][C:7]=1[NH2:18]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24479Stannous ChlorideHCID 58683729HCID 58683729, compound

Product 1

HCID 68536089HCID 68536089, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(E)-3-[4Chloro-5-(2-methoxyethoxy)-2-nitrophenyl]-acrylic acid methyl ester (910 mg; 2.88 mmol) was dissolved in MeOH (160 ml)/HClconc (50 ml). SnCl2 (7.4 g; 39 mmol) was added and the reaction mixture stirred for 1 h at room temperature, poured on saturated Na2CO3 and extracted with TBME three times. The combined organic phases were dried over Na2SO4 and evaporated to dryness to yield the intermediate (E)-3-[2-amino-4-chloro-5-(2-methoxyethoxy)-phenyl]acrylic acid methyl ester (740 mg; 90%).

Workup

  1. extractionextracted with TBME three times
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-7a826c72dd8c4de0a50b28ebec298994
Source dataset
uspto-grants-2010_01
Patent number
US07645760B2

Reaction notes

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