4-Nitrobenzoyl chloride → HCID 18354599, compound

HRID 1292137Notes

Reaction equation

HRID 1292137 reaction equation
[NH2:1][C:2]1[C:11]([OH:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[N+:13]([C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1)([O-:15])=[O:14]>C1(C)C=CC=C(C)C=1>[OH:12][C:11]1[C:2]([NH:1][C:20](=[O:21])[C:19]2[CH:18]=[CH:17][C:16]([N+:13]([O-:15])=[O:14])=[CH:24][CH:23]=2)=[C:3]([CH:8]=[CH:9][CH:10]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 85024-Nitrobenzoyl chlorideHCID 205248Anthranilic acid, 3-hydroxy-, methyl ester

Product 1

HCID 18354599HCID 18354599, compound

Reagents, catalysts & solvents 1

HCID 7929M-XyleneSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 2-amino-3-hydroxybenzoate (0.5 g; 2.99 mmol) was dissolved in m-xylene (40 ml) with warming to 60° C. 4-Nitrobenzoyl chloride (0.556 ml; 2.99 mmol) was added dropwise, and this was left to stir for 4 hours. The solution was cooled to ambient temperature and the m-xylene removed under reduced pressure. The solid was dissolved in water (100 ml) and the organics extracted into ethyl acetate (3×50 ml). The organic fractions were pooled, dried over magnesium sulphate, filtered and the solvent removed under reduced pressure.

Workup

  1. waitthis was left
  2. temperatureThe solution was cooled to ambient temperature
  3. customthe m-xylene removed under reduced pressure
  4. dissolutionThe solid was dissolved in water (100 ml)
  5. extractionthe organics extracted into ethyl acetate (3×50 ml)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-6969f2d40bab4d2990ba48a3e407df41
Source dataset
uspto-grants-1998_05
Patent number
US05756510

Reaction notes

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