Hydrochloric Acid → 2-[(1,2,3,4-tetrahydro-5-hydroxy-2-naphthyl)methyl]-6-diphenylmethyl-3(2H)-pyridazinone

HRID 963700Notes

Reaction equation

HRID 963700 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH:7]([CH2:13][N:14]1[C:19](=[O:20])[CH:18]=[CH:17][C:16]([CH:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:15]1)[CH2:8]2.B(Br)(Br)Br.Cl>ClCCl>[OH:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH:7]([CH2:13][N:14]1[C:19](=[O:20])[CH:18]=[CH:17][C:16]([CH:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[N:15]1)[CH2:8]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 701861932-[(1,2,3,4-tetrahydro-5-methoxy-2-naphthyl)methyl]-6-diphenylmethyl-3(2H)-pyridazinone

Product 1

HCID 701861852-[(1,2,3,4-tetrahydro-5-hydroxy-2-naphthyl)methyl]-6-diphenylmethyl-3(2H)-pyridazinoneYield 75.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-[(1,2,3,4-tetrahydro-5-methoxy-2-naphthyl)methyl]-6-diphenylmethyl-3(2H)-pyridazinone (0.60 g) in dry dichloromethane (5 ml) was added dropwise 1N boron tribromide in dichloromethane (1.5 ml) under ice bath cooling. The mixture was stirred at the same temperature for 2.5 hours. The mixture was poured into 1N hydrochloric acid and extracted with ethyl acetate. The extract was separated, washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane: ethyl acetate=1:1) to give 2-[(1,2,3,4-tetrahydro-5-hydroxy-2-naphthyl)methyl]-6-diphenylmethyl-3(2H)-pyridazinone (0.44 g) as a pale yellow oil.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. customThe extract was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (n-hexane: ethyl acetate=1:1)

Sources & evidence

ORD record
ord-214de5bd81474bcb9580d18f181aaf94
Source dataset
uspto-grants-1998_06
Patent number
US05763489

Reaction notes

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