Sodium Hydroxide → HCID 59811938, compound

HRID 2114045Notes

Reaction equation

HRID 2114045 reaction equation
CN(C)C([N:5]1[C:9]2=[N:10][CH:11]=[C:12]([Br:14])[CH:13]=[C:8]2[C:7]([C:15]2[O:19][CH:18]=[N:17][CH:16]=2)=[CH:6]1)=O.[OH-].[Na+]>CCO>[Br:14][C:12]1[CH:13]=[C:8]2[C:7]([C:15]3[O:19][CH:18]=[N:17][CH:16]=3)=[CH:6][NH:5][C:9]2=[N:10][CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11724479HCID 11724479, compound

Product 1

HCID 59811938HCID 59811938, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 21 (667 mg, 1.99 mmol), EtOH (20 mL) and 10% aq. NaOH (10 mL) was heated at 90° C. for 40 min then cooled and poured onto water (50 mL). The aqueous layer was extracted with ethyl acetate (4×40 mL). The combined organic extracts were washed with brine (30 mL), dried (MgSO4) and concentrated to give 22 as a white solid (477 mg, 91%); 1H NMR (400 MHz, CDCl3) δ 7.27 (d, J=2.5 Hz, 1H), 7.67 (d, J=2.5 Hz, 1H), 7.94 (s, 1H), 8.33 (d, J=2.1 Hz, 1H), 8.44 (d, J=2.1 Hz, 1H), 9.30-9.10 (bs, NH).

Workup

  1. temperaturethen cooled
  2. additionpoured onto water (50 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (4×40 mL)
  4. washThe combined organic extracts were washed with brine (30 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-546ee867f2164b29ac50e888f7280f9e
Source dataset
uspto-grants-2008_10
Patent number
US07432375B2

Reaction notes

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