Sodium Methoxide → HCID 58349464, compound

HRID 2090058

Reaction equation

HRID 2090058 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([Cl:13])[N:6]=[C:7]2Cl.[CH3:14][O-:15].[Na+]>O>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([Cl:13])[N:6]=[C:7]2[O:15][CH3:14]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 205790315-Bromo-1,3-dichloroisoquinoline

Product 1

HCID 58349464HCID 58349464, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 5-bromo-1,3-dichloroisoquinoline (580 mg, 2.1 mmol) and NaOMe (0.5 M in MeOH, 5.0 mL, 2.5 mmol) was heated at 70° C. for one hour. The mixture was poured into water then extracted with EtOAc. The organic layer was dried over Na2SO4, filtered, then concentrated to afford the title compound: 1H NMR (500 MHz, CDCl3): δ 8.23 (d, J=9.0 Hz, 1H), 7.96 (d, J=7.5 Hz, 1H); 7.65 (s, 1H), 7.39 (t, J=8.5 Hz, 1H), 4.20 (s, 3H). LC6: 3.86 min. (M+H) 272.

Workup

  1. extractionthen extracted with EtOAc
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cbfb59c070f04809b4bad679f770f86d
Source dataset
uspto-grants-2013_05
Patent number
US08436015B2

Linked notes

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