Anthranilic Acid → Anthranilic acid, N-o-nitrophenyl-

HRID 1747425Notes

Reaction equation

HRID 1747425 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH2:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([OH:16])=[O:15].C([O-])([O-])=O.[Na+].[Na+].O>CC(O)=O>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([OH:16])=[O:15])([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 227Anthranilic AcidHCID 962WaterHCID 10340Sodium CarbonateHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 101319Anthranilic acid, N-o-nitrophenyl-Yield 43.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

1-Fluoro-2-nitro-benzene (0.53 mL, 5.0 mmol), 2-Amino-benzoic acid (750 mg, 5.5 mmol) and Na2CO3 (420 mg, 4.0 mmol) are added together in reaction flask and the mixture is heated at 130° C. for 60 hrs. After it is cooled down to room temperature, 50 mL of water is added and HOAc is used to adjust the pH to slightly acidic. Then the mixture is extracted with EtOAc (3×50 mL) and the organic layers are combined, washed with water (3×50 mL), dried (Na2SO4) and concentrated to give crude product. Purifiction by flash column chromatography affords 560 mg (43%) of 2-(2-Nitro-phenylamino)-benzoic acid.

Workup

  1. temperatureAfter it is cooled down to room temperature
  2. extractionThen the mixture is extracted with EtOAc (3×50 mL)
  3. washwashed with water (3×50 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto give crude product

Sources & evidence

ORD record
ord-19605f1be5e54af0be4d5a505d93bcc8
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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