Potassium Carbonate → HCID 67252349, compound

HRID 2427675Notes

Reaction equation

HRID 2427675 reaction equation
[CH:1]1([NH:4]C)[CH2:3][CH2:2]1.CO[C:8](=[O:19])[C:9]1[C:14]([I:15])=[CH:13][C:12]([Cl:16])=[CH:11][C:10]=1[CH2:17]Br.[C:20]([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[CH:1]1([N:4]2[CH:17]([CH3:20])[C:10]3[C:9](=[C:14]([I:15])[CH:13]=[C:12]([Cl:16])[CH:11]=3)[C:8]2=[O:19])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11029756N-MethylcyclopropanamineHCID 67251492HCID 67251492, compound

Product 1

HCID 67252349HCID 67252349, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of cyclopropyl-methylamine (1.3 mmol, 0.111 mL), 2-bromomethyl-4-chloro-6-iodo-benzoic acid methyl ester (0.389 g, 1.0 mmol), and K2CO3 (0.277 g, 2 mmol) in toluene (4 mL) was heated with stirring at 100° C. for 2 h. The resulting mixture was filtered and concentrated. Silica gel column chromatography using 30% ethyl acetate in hexane afforded 2-Cyclopropyl methyl-5-chloro-7-iodo-2,3-dihydro-isoindol-1-one (0.123 g, 35%). 1H NMR (300 MHz, CDCl3): δ (ppm) 0.32 (m, 2H), 0.60 (m, 2H), 1.04 (m, 1H), 3.46 (d, 2H), 4.36 (s, 2H), 7.43 (s, 1H), 7.90 (s, 1H). GC-MS: m/z 347 (M)+0.332 (M−15)+

Workup

  1. temperaturewas heated
  2. filtrationThe resulting mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5669afc2e73f41b09728e1d7d416c321
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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