3-Methoxyaniline → HCID 11472361, compound

HRID 2113640Notes

Reaction equation

HRID 2113640 reaction equation
[CH3:1][C:2]([CH3:15])([CH3:14])[CH:3]=[CH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1.C(Cl)(=O)C(Cl)=O.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([NH2:30])[CH:25]=1>CCOC(C)=O.CN(C=O)C>[CH3:14][C:2]([CH3:1])([CH3:15])/[CH:3]=[CH:4]/[C:5]1[CH:6]=[CH:7][C:8]([C:9]([NH:30][C:26]2[CH:27]=[CH:28][CH:29]=[C:24]([O:23][CH3:22])[CH:25]=2)=[O:11])=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 108243-MethoxyanilineHCID 65578Oxalyl chlorideHCID 57299654HCID 57299654, compound

Product 1

HCID 11472361HCID 11472361, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a cooled (0° C.) and well stirred suspension of 4-(3,3-dimethyl-but-1-enyl)-benzoic acid (1.5 g, 7.34 mMol) in a mixture of EtOAc and DMF (1:1, 25 mL) is added oxalyl chloride (0.364 g, 4.04 mMol) slowly drop-wise and the mixture is agitated for one hour. m-Anisidine (1.36 g, 11.01 mMol) is then added in EtOAc (5 mL) and the mixture is stirred for 6.0 hours before being quenched with saturated potassium carbonate solution. The precipitate is filtered, washed with water and vacuum dried to obtain the title compound.

Workup

  1. temperatureTo a cooled
  2. stirringthe mixture is stirred for 6.0 hours
  3. custombefore being quenched with saturated potassium carbonate solution
  4. filtrationThe precipitate is filtered
  5. washwashed with water and vacuum
  6. customdried

Sources & evidence

ORD record
ord-7fa7a1ad03cf4adaa4cd8bcb9acf4644
Source dataset
uspto-grants-2008_10
Patent number
US07432281B2

Reaction notes

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