1-Propanol → N-carbopropoxymethylene-4-chloro-anthranilic acid

HRID 1741348Notes

Reaction equation

HRID 1741348 reaction equation
[C:1]([CH:4]=[N:5][C:6]1[C:7](=[CH:11][CH:12]=[C:13]([Cl:15])[CH:14]=1)[C:8]([OH:10])=[O:9])([OH:3])=[O:2].OS(O)(=O)=O.[CH2:21](O)[CH2:22][CH3:23]>>[C:1]([CH:4]=[N:5][C:6]1[C:7](=[CH:11][CH:12]=[C:13]([Cl:15])[CH:14]=1)[C:8]([OH:10])=[O:9])([O:3][CH2:21][CH2:22][CH3:23])=[O:2]

Participants

4

Reactant 3

HCID 10311-PropanolHCID 1118Sulfuric AcidHCID 19597249HCID 19597249, compound

Product 1

HCID 21835791N-carbopropoxymethylene-4-chloro-anthranilic acidYield 61%

Conditions

Temperature
70 °C

Procedure

5 g (21.8 mmol) of N-carboxymethylene-4-chloro-anthranilic acid are dissolved in 40 ml of n-propanol, 108 mg (1.05 mmol) of concentrated H2SO4 are added and the mixture is heated at 70° C. for 4.5 hours. It is then cooled to room temperature and the product which has precipitated out is filtered off with suction and washed with n-propanol. After drying, 3.6 g (13.3 mmol; 61%) of N-carbopropoxymethylene-4-chloro-anthranilic acid are obtained as a pale yellow solid.

Workup

  1. temperatureIt is then cooled to room temperature
  2. customthe product which has precipitated out
  3. filtrationis filtered off with suction
  4. washwashed with n-propanol
  5. customAfter drying

Sources & evidence

ORD record
ord-40cf2da725fc42e5af523ac22019e95c
Source dataset
uspto-grants-1999_10
Patent number
US05973189

Reaction notes

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