Hydrochloric Acid → HCID 57440609, compound

HRID 1011444Notes

Reaction equation

HRID 1011444 reaction equation
[CH:1]([C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[NH:11][C:12](=O)OC(C)(C)C)=O.CO/C=[CH:22]/[C:23]([O:25][CH3:26])=[O:24].Cl.C([O-])([O-])=O.[Na+].[Na+]>CO>[CH3:10][O:9][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[CH:1]=[C:22]([C:23]([O:25][CH3:26])=[O:24])[CH:12]=[N:11]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 5323651Methyl 3-methoxyacrylateHCID 22897235HCID 22897235, compound

Product 1

HCID 57440609HCID 57440609, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl N-(2-formyl-3-methoxyphenyl)carbamate (7.8 g, 31 mmol) [described in Adv. Synth. Catal. 2003, 345, 743-765] and methyl trans-3-methoxyacrylate (7.4 mL, 68.4 mmol) dissolved in 150 ml of methanol, was added slowly 100 mL of an aqueous solution of hydrochloric acid 3M. The resulting mixture was stirred under reflux for 3 hours. The reaction mixture was then cooled to room temperature and neutralised by adding Na2CO3. The aqueous solution was extracted with CH2Cl2 (4×150 mL). The combined organic layers were dried over MgSO4, filtered and evaporated under vacuum. The crude product was then filtered on silica gel (AcOEt:cyclohexane/1:1) to afford 5.6 g of compound of molecular formula C12H11NO3. Aspect: yellow powder.

Workup

  1. temperatureunder reflux for 3 hours
  2. extractionThe aqueous solution was extracted with CH2Cl2 (4×150 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated under vacuum
  6. filtrationThe crude product was then filtered on silica gel (AcOEt:cyclohexane/1:1)

Sources & evidence

ORD record
ord-0c96656498674307936e64d21f7dd9ab
Source dataset
uspto-grants-2011_07
Patent number
US07977354B2

Reaction notes

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