Acetic Acid → [5-Ethoxy-2-(1,4,5,7-tetramethyl-pyrrolo[3,4-d]pyridazin-6-yl)-phenyl]-methanol

HRID 2375420Notes

Reaction equation

HRID 2375420 reaction equation
[C:1]([CH:4]([C:12](=O)[CH3:13])[CH:5]([C:9](=O)[CH3:10])[C:6](=O)[CH3:7])(=O)[CH3:2].[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH3:24])=[CH:18][C:17]=1[CH2:25][OH:26].CC(O)=O.[NH2:31][NH2:32]>CCO>[CH2:23]([O:22][C:19]1[CH:20]=[CH:21][C:16]([N:15]2[C:1]([CH3:2])=[C:4]3[C:5]([C:9]([CH3:10])=[N:31][N:32]=[C:12]3[CH3:13])=[C:6]2[CH3:7])=[C:17]([CH2:25][OH:26])[CH:18]=1)[CH3:24]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 9321HydrazineHCID 787303,4-Diacetyl-2,5-hexanedioneHCID 45091061(2-Amino-5-ethoxyphenyl)methanol

Product 1

HCID 10404055[5-Ethoxy-2-(1,4,5,7-tetramethyl-pyrrolo[3,4-d]pyridazin-6-yl)-phenyl]-methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1,1,2,2-tetraacetylethane (600 mg, 3.0 mol) and (2-amino-5-ethoxy-phenyl)-methanol (496 mg, 3.0 mmol) was refluxed in EtOH (10 mL)/AcOH (1%) for 14 h. It was cooled to rt, and anhydrous hydrazine (200 μL, 6.3 mmol) was added. After stirring at rt for 1 h, the reaction mixture was poured into ice water (50 mL). The resulting precipitate was filtered, washed with diethyl ether (20 mL), and then dried under vacuum to afford [5-ethoxy-2-(1,4,5,7-tetramethyl-pyrrolo[3,4-d]pyridazin-6-yl)-phenyl]-methanol as a pale yellow solid: 1H NMR (CDCl3, 500 MHz) δ 7.22 (s, 1H), 6.95 (m, 2H), 4.40 (s, 2H), 4.16 (q, 2H), 2.66 (s, 6H), 2.41 (s, 6H), 1.50 (t, 3H); MS (ESI) 326 (M+H)+.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with diethyl ether (20 mL)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-488a35467d4e44b18e97a2c0880aa63f
Source dataset
uspto-grants-2008_12
Patent number
US07465730B2

Reaction notes

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