Hydrochloric Acid → 5-Carbamoyl-2-methoxybenzoic acid

HRID 558340Notes

Reaction equation

HRID 558340 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:13][CH3:14])=[C:7]([CH:12]=1)[C:8]([O:10]C)=[O:9])#[N:2].[OH-:15].[Na+].Cl>CS(C)=O.O>[CH3:14][O:13][C:6]1[C:7]([C:8]([OH:10])=[O:9])=[CH:12][C:3]([C:1]([NH2:2])=[O:15])=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18464789Methyl 5-cyano-2-methoxybenzoate

Product 1

HCID 132228085-Carbamoyl-2-methoxybenzoic acidYield 63%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 5-cyano-2-methoxybenzoate (2 g) prepared in step A was dissolved in 24 mL of dimethyl sulfoxide, and 12 mL of a 1 M aqueous solution of sodium hydroxide was added. After stirring for 4 hours and a half at 80° C., the mixture was cooled in an ice bath, and adjusted to pH of about 4 with the use of 10 mL of 1 M hydrochloric acid. The resulting solution was diluted with 200 mL of water, and cooled for several hours in a refrigerator. The precipitate formed was separated by filtration, washed with cold water, and then dried over diphosphorus pentoxide under reduced pressure to obtain 1.3 g (63%) of 6-methoxyisophthalamic acid.

Workup

  1. temperaturecooled for several hours in a refrigerator
  2. customThe precipitate formed
  3. customwas separated by filtration
  4. washwashed with cold water
  5. dry with materialdried over diphosphorus pentoxide under reduced pressure

Sources & evidence

ORD record
ord-3521f9e2e3d94fbc90605ca67d4de63b
Source dataset
uspto-grants-2011_11
Patent number
US08063046B2

Reaction notes

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