Hydrazine → 2-chloro-4-(1,4,5,7-tetramethyl-pyrrolo[3,4-d]pyridazin-6-yl)-phenol

HRID 2375385Notes

Reaction equation

HRID 2375385 reaction equation
[C:1]([C:4]1[C:5]([C:19](=O)[CH3:20])=[C:6]([CH3:18])[N:7]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([Cl:17])[CH:11]=2)[C:8]=1[CH3:9])(=O)[CH3:2].[NH2:22][NH2:23]>>[Cl:17][C:12]1[CH:11]=[C:10]([N:7]2[C:8]([CH3:9])=[C:4]3[C:5]([C:19]([CH3:20])=[N:22][N:23]=[C:1]3[CH3:2])=[C:6]2[CH3:18])[CH:15]=[CH:14][C:13]=1[OH:16]

Participants

3

Reactant 2

HCID 9321HydrazineHCID 69275407HCID 69275407, compound

Product 1

HCID 104476182-chloro-4-(1,4,5,7-tetramethyl-pyrrolo[3,4-d]pyridazin-6-yl)-phenol

Procedure

To a solution of 1-[4-acetyl-1-(3-chloro-4-hydroxy-phenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-ethanone (340 mg, 1.0 mmol) was added hydrazine (50 μL). After stirring at rt for 1 h, the reaction mixture was poured into ice water (25 mL). The resulting precipitate was filtered, washed with diethyl ether (20 mL), and then dried under vacuum to afford 2-chloro-4-(1,4,5,7-tetramethyl-pyrrolo[3,4-d]pyridazin-6-yl)-phenol as a pale yellow solid: 1H NMR (CD3OD, 500 MHz) δ 7.34 (br s, 1H), 7.08 (m, 2H), 2.83 (s, 6H), 2.52 (s, 6); MS (ESI) 302 (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-be8c377369ae468bbbfb32d2ddeda999
Source dataset
uspto-grants-2008_12
Patent number
US07465730B2

Reaction notes

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