1-Butanol → HCID 18789556, compound

HRID 355776Notes

Reaction equation

HRID 355776 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:6]([CH:20]=1)[CH2:7][N:8]([C:11]1[N:16]=[N:15][C:14]([C:17](N)=[O:18])=[CH:13][CH:12]=1)[CH2:9][CH3:10].[OH-].[Na+].C([OH:35])CCC>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:6]([CH:20]=1)[CH2:7][N:8]([C:11]1[N:16]=[N:15][C:14]([C:17]([OH:35])=[O:18])=[CH:13][CH:12]=1)[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 14798Sodium HydroxideHCID 18789581HCID 18789581, compound

Product 1

HCID 18789556HCID 18789556, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-[N-(5-bromo-2-benzylaminobenzyl)-N-ethylamino]pyridazine-3-carboxamide (700 mg, 1.59 mmol), sodium hydroxide pellets (200 mg, 5.0 mmol) and butanol was stirred at reflux for 3 hours. The mixture was cooled, diluted with water (100 ml) and washed with hexane (2×100 ml). The aqueous layer was acidified with formic acid and extracted with dichloromethane (2×200 ml). The combined organic extracts were dried over anhydrous magnesium sulphate and evaporated to give a white solid, which was triturated with ether and filtered to give the title compound (500 mg).

Workup

  1. temperatureat reflux for 3 hours
  2. temperatureThe mixture was cooled
  3. washwashed with hexane (2×100 ml)
  4. extractionextracted with dichloromethane (2×200 ml)
  5. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulphate
  6. customevaporated
  7. customto give a white solid, which
  8. customwas triturated with ether
  9. filtrationfiltered

Sources & evidence

ORD record
ord-66ff1c2396174c21bf81038ee38a8bcb
Source dataset
uspto-grants-1998_11
Patent number
US05834468

Reaction notes

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