Water → HCID 136127068, compound

HRID 1896769Notes

Reaction equation

HRID 1896769 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([NH2:9])=[CH:6][C:7]=1[CH3:8].[NH2:11][C:12]1[CH:20]=[CH:19][C:15]([C:16](O)=O)=[C:14]([OH:21])[CH:13]=1.O>C(OCC)(=O)C>[NH2:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]2[NH:10][C:4]3[CH:3]=[C:2]([CH3:1])[C:7]([CH3:8])=[CH:6][C:5]=3[N:9]=2)=[C:14]([OH:21])[CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 46494-Aminosalicylic AcidHCID 766354,5-Dimethyl-1,2-phenylenediamine

Product 1

HCID 136127068HCID 136127068, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

To polyphosphoric acid at 130° C. were added 4,5-dimethylbenzene-1,2-diamine (500 mg, 3.67 mmol) and 4-amino-2-hydroxybenzoic acid (562 mg, 3.67 mmol), and the resulting mixture was then heated to 130° C. for 16 h. The solution was then poured into water and the resulting precipitate was dissolved in ethyl acetate and washed with Na2CO3. The aqueous layer was separated and extracted twice with ethyl acetate. The combined organic layers were dried over anhydrous MgSO4 and evaporated. The resulting solid was purified by column chromatography eluting with ethyl acetate/hexanes 50:50 v/v to afford 260 mg (28%) of the title compound (LCMS RT=6.14 min, MH+ 254.1)

Workup

  1. washwashed with Na2CO3
  2. customThe aqueous layer was separated
  3. extractionextracted twice with ethyl acetate
  4. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  5. customevaporated
  6. customThe resulting solid was purified by column chromatography
  7. washeluting with ethyl acetate/hexanes 50:50 v/v

Sources & evidence

ORD record
ord-7122fea4fa134564bc490414a56ea8ca
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Reaction notes

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