Hydrochloric Acid → 5-Chloro-2-(methylamino)benzoic acid

HRID 2244347Notes

Reaction equation

HRID 2244347 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6](C)[C:7](=O)[O:8][C:9](=[O:10])[C:4]=2[CH:3]=1.Cl>[OH-].[K+]>[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([NH:6][CH3:7])=[C:4]([CH:3]=1)[C:9]([OH:10])=[O:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 267242H-3,1-Benzoxazine-2,4(1H)-dione, 6-chloro-1-methyl-

Product 1

HCID 125113245-Chloro-2-(methylamino)benzoic acidYield 95.4%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 3.955 g of 6-chloro-1-methyl-1H-benzo[d][1,3]oxazine-2,4-dione (18.69 mmol) in 37 ml of 2N KOH was heated to 100° C. for 4 h. The clear solution was then allowed to cool to RT and the pH was adjusted to 6-7 by addition of 3N HCl. The precipitate formed was filtered off and dried to give 3.31 g (95%) of the title compound as a yellow solid. MS (ISP) 183.9 (M−H)−.

Workup

  1. temperatureto cool to RT
  2. customThe precipitate formed
  3. filtrationwas filtered off
  4. customdried

Sources & evidence

ORD record
ord-46b7831bebdc428cbff2eac2af989f10
Source dataset
uspto-grants-2010_03
Patent number
US07678818B2

Reaction notes

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