Ammonia → HCID 178508198, compound

HRID 537161Notes

Reaction equation

HRID 537161 reaction equation
[N:1]#[C:2]Br.[NH2:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[NH2:15])[C:8]([O:10]C)=[O:9].N.Cl>O.C(OCC)(=O)C>[NH2:1][C:2]1[NH:15][C:14]2[CH:13]=[CH:12][C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]=2[N:4]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 10476Cyanogen BromideHCID 1355243,5-Diamino-2-methylbenzoic acid

Product 1

HCID 178508198HCID 178508198, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of cyanogen bromide (5.0 mL, 5 M in acetonitrile, 25 mmol) was added to a mixture of methyl 3,4-diaminobenzoate (3.0 g, 18 mmol) in water (50 mL). The reaction was stirred at room temperature overnight. Aqueous ammonia (20 mL) and ethyl acetate (100 mL) were added to the reaction mixture and the layers were separated. The organics were dried over sodium sulfate, filtered, and concentrated. To the crude residue was added 2 N aqueous hydrochloric acid (18 mL, 36.0 mmol) and the mixture was heated at reflux overnight. The reaction was concentrated to give the title compound (2.90 g, 97%). 1H NMR (400 MHz, DMSO-d6, δ): 8.75 (s, 2H), 7.84 (s, 1H), 7.77 (dd, J=1.2, 8.4 Hz, 1H), 7.38 (d, J=8.4 Hz, 1H).

Workup

  1. customthe layers were separated
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. temperaturethe mixture was heated
  6. temperatureat reflux overnight
  7. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-291544cc1c024d82b1b40d8524b86025
Source dataset
uspto-grants-2014_10
Patent number
US08859773B2

Reaction notes

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