1H-Isoindole-1,3(2H)-dione, 2-(6-chloro-4,5-dimethyl-2-pyridinyl)- → 6-Chloro-4,5-dimethylpyridin-2-amine

HRID 869893Notes

Reaction equation

HRID 869893 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]2C(=O)C3C(=CC=CC=3)C2=O)[CH:5]=[C:4]([CH3:19])[C:3]=1[CH3:20]>N.CO.O>[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[C:4]([CH3:19])[C:3]=1[CH3:20]

Participants

5

Reactant 1

HCID 748886471H-Isoindole-1,3(2H)-dione, 2-(6-chloro-4,5-dimethyl-2-pyridinyl)-

Product 1

HCID 735538296-Chloro-4,5-dimethylpyridin-2-amineYield 46%

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 2-(6-chloro-4,5-dimethylpyridin-2-yl)isoindoline-1,3-dione (650 mg, 2.27 mmol) in ammonia in methanol (2 M, 50 mL) was stirred at the room temperature overnight. The mixture was diluted with water (50 mL) and extracted with ethyl acetate (50 mL×3). The combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated under vacuum to give a crude residue that was purified by silica gel column chromatography (10-15% ethyl acetate in petroleum ether) to give 6-chloro-4,5-dimethylpyridin-2-amine (160 mg, 46%). 1H NMR (300 MHz, d-DMSO) δ 6.21 (s, 1H), 5.93 (brs, 2H), 2.11 (s, 3H), 2.05 (s, 3H). MS (ESI) m/z (M+H+): 157.2.

Workup

  1. extractionextracted with ethyl acetate (50 mL×3)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customevaporated under vacuum
  5. customto give a crude residue that
  6. customwas purified by silica gel column chromatography (10-15% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-334c52a084354b32934a6d77ba53eac6
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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