Chlorosuccinimide → HCID 68863981, compound

HRID 1725914Notes

Reaction equation

HRID 1725914 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:12]([O:14][CH3:15])=[O:13].[Cl:16]N1C(=O)CCC1=O>C(#N)C>[NH2:1][C:2]1[C:11]([Cl:16])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 68862599HCID 68862599, compound

Product 1

HCID 68863981HCID 68863981, compoundYield 32.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 2-amino-1-naphthoate (0.7 g, 3.48 mmol) in acetonitrile (15 mL) was treated with N-chlorosuccinimide (490 mg, 3.65 mmol), stirred at 60° C. for 7 hours, cooled to room temperature, stirred overnight, concentrated, and purified by flash column chromatography on silica gel with 10% ethyl acetate/n-hexane to provide the desired product (270 mg). MS (ESI(−)) m/e 234 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 8.13 (s, 1H), 8.10 (d, 1H), 7.75 (d, 1H), 7.46 (dt, 1H), 7.26 (dt, 1H), 6.62 (s, 2H), 3.95 (s, 3H).

Workup

  1. temperaturecooled to room temperature
  2. stirringstirred overnight
  3. concentrationconcentrated
  4. custompurified by flash column chromatography on silica gel with 10% ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-9ea6275c229a4a64b1fe7f0d65311244
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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