Hydrochloric Acid → HCID 67531613, compound

HRID 240367Notes

Reaction equation

HRID 240367 reaction equation
C1(C(C2C=CC=CC=2)=[N:8][C:9]2[C:10]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]=3)=[CH:11][CH:12]=[CH:13][CH:14]=2)C=CC=CC=1.Cl>O1CCCC1>[CH3:22][C:18]1[N:17]=[C:16]([NH:15][C:10]2[C:9]([NH2:8])=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86643866HCID 86643866, compound

Product 1

HCID 67531613HCID 67531613, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

42.1 g (0.11 mol) of N1-(diphenylmethylene)-N2-(6-methylpyridine-2-yl)benzene-1,2-diamine was dissolved in tetrahydrofuran (100 ml), and 10% hydrochloric acid (45 ml) was added thereto, and was stirred for 2 hours at room temperature. The solvent was distilled off under reduced pressure, and water was added to the residue thus obtained and washed with ethyl acetate. Then, the aqueous layer was adjusted to pH>11, and the aqueous layer was extracted with methylene chloride. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to obtain 19.8 g (yield: 83%) of N-(6-methylpyridine-2-yl)benzene-1,2-diamine.

Workup

  1. distillationThe solvent was distilled off under reduced pressure, and water
  2. additionwas added to the residue
  3. customthus obtained
  4. washwashed with ethyl acetate
  5. extractionthe aqueous layer was extracted with methylene chloride
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-622a66632f66408f8cefde188b033613
Source dataset
uspto-grants-2014_02
Patent number
US08648075B2

Reaction notes

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