N-(3-amino-4-methylphenyl)acetamide → HCID 67271594, compound

HRID 1696456Notes

Reaction equation

HRID 1696456 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=O)C)[CH:5]=[CH:6][C:7]=1[CH3:8].[Cl:13]C1[N:19]=[CH:18][CH:17]=[CH:16][N:15]=1>CN(C=O)C>[ClH:13].[CH3:8][C:7]1[C:2]([NH2:1])=[CH:3][C:4]([NH:9][C:10]2[N:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 22865N-(3-amino-4-methylphenyl)acetamideHCID 744042-Chloropyrimidine

Product 1

HCID 67271594HCID 67271594, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N-(3-amino-4-methyl-phenyl)acetamide (5 g, 25 mmol) in DMF (5 mL) was added 2-chloropyrimidine (3.8 g, 33 mmol) and KI (0.5 g). The reaction was stirred at 100° C. overnight, cooled to 10° C. (100 mL). The resulting mixture was extracted with CH2Cl2 (2×100 mL). The combined organic layers were dried (Na2SO4) and concentrated under vacuum. The residue was dissolved in conc. HCl (10 mL), stirred at 80° C. for 2 h and concentrated under vacuum to yield 6-methyl-N′-(pyrimidin-2-yl)benzene-1,3-diamine hydrochloride (3.75 g, 75% yield). 1H NMR (400 MHz, CDCl3): 8.36 (dd, J=15.2, 4.8 Hz, 2H), 7.46 (d, J=2.4 Hz, 1H), 6.97 (d, J=8.0 Hz, 1H), 7.26 (s, 1H), 6.67 (t, J=4.8 Hz, 1H), 6.39 (dd, J=8.0, 2.4, Hz, 1H), 2.20 (s, 3H); MS (ESI) m/e: 201 (M+H+).

Workup

  1. temperaturecooled to 10° C. (100 mL)
  2. extractionThe resulting mixture was extracted with CH2Cl2 (2×100 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated under vacuum
  5. dissolutionThe residue was dissolved in conc. HCl (10 mL)
  6. stirringstirred at 80° C. for 2 h
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7b1e20b4663047918c3fc8ce423f7f9f
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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