Hydrochloric Acid → HCID 67531613, compound

HRID 1942164Notes

Reaction equation

HRID 1942164 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-fcb05ea5e5454eb38858e0ccd85db281
Source dataset
uspto-grants-2013_03
Patent number
US08389523B2

Reaction notes

Loading…