Ammonia → HCID 70896199, compound

HRID 2403674Notes

Reaction equation

HRID 2403674 reaction equation
[N:1]#[C:2]Br.N[C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1N)[C:8]([O:10]C)=[O:9].[NH3:16].Cl.[C:18]([O:21]CC)(=O)[CH3:19]>O>[C:18]([C:19]1[NH:1][C:2]2[C:14]([CH:5]=1)=[CH:13][CH:12]=[C:7]([C:8]([OH:10])=[O:9])[CH:6]=2)(=[O:21])[NH2:16]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 10476Cyanogen BromideHCID 1355243,5-Diamino-2-methylbenzoic acid

Product 1

HCID 70896199HCID 70896199, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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, 2 H), 7.84 (s, 1 H), 7.77 (dd, J=1.2 Hz, J=8.4 Hz, 1 H), 7.38 (d, J=8.4 Hz, 1 H).

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-61d21ee3e309485d8892b2557514d0e3
Source dataset
uspto-grants-2014_08
Patent number
US08802688B2

Reaction notes

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