Carbon Dioxide → HCID 13894021, compound

HRID 859120Notes

Reaction equation

HRID 859120 reaction equation
C([Li])CCC.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17].[C:21](=[O:23])=[O:22].Cl>O1CCCC1>[CH3:6][O:7][C:8]1[C:9]([NH:14][C:15](=[O:20])[C:16]([CH3:17])([CH3:19])[CH3:18])=[C:10]([CH:11]=[CH:12][CH:13]=1)[C:21]([OH:23])=[O:22]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 4100598HCID 4100598, compoundHCID 178418339Butyllithium

Product 1

HCID 13894021HCID 13894021, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyllithium (1.6M solution in hexane; 200 ml, 0.32 mol) was added dropwise under nitrogen at −10° C. to a stirred solution of N-(2-methoxyphenyl)pivalamide (27.6 g, 0.133 mol) in tetrahydrofuran (600 ml), the mixture was allowed to warm to ambient temperature, stirred for a further 2 hours, then it was added to a large excess of crushed solid carbon dioxide. The mixture was allowed to warm to ambient temperature, 3M hydrochloric acid (200 ml) was added and the tetrahydrofuran was removed in vacuo. The resulting solid was collected by filtration and crystallised from acetonitrile to give 3-methoxy-2-pivalamidobenzoic acid (21 g; 63%) as a solid, m.pt. 117–120° C. Concentration of the liquor yielded a second crop (2.6 g; 8%).

Workup

  1. temperatureto warm to ambient temperature
  2. customthe tetrahydrofuran was removed in vacuo
  3. filtrationThe resulting solid was collected by filtration
  4. customcrystallised from acetonitrile

Sources & evidence

ORD record
ord-b8098ca06cd14e54be0afa1310ad9d7a
Source dataset
uspto-grants-2006_12
Patent number
US07151102B2

Reaction notes

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