Boron tribromide → 8-hydroxy-5,6-dihydro-3H-benzo[f]cinnolin-2-one

HRID 2042642Notes

Reaction equation

HRID 2042642 reaction equation
C[O:2][C:3]1[CH:17]=[CH:16][C:6]2[C:7]3[C:12]([CH2:13][CH2:14][C:5]=2[CH:4]=1)=[N:11][NH:10][C:9](=[O:15])[CH:8]=3.B(Br)(Br)Br.[NH4+].[Cl-]>C(Cl)Cl>[OH:2][C:3]1[CH:17]=[CH:16][C:6]2[C:7]3[C:12]([CH2:13][CH2:14][C:5]=2[CH:4]=1)=[N:11][NH:10][C:9](=[O:15])[CH:8]=3

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 25517Ammonium ChlorideHCID 596519778-methoxy-5,6-dihydro-3H-benzo[f]cinnolin-2-one

Product 1

HCID 596519348-hydroxy-5,6-dihydro-3H-benzo[f]cinnolin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a 100 mL round bottom flask, 8-methoxy-5,6-dihydro-3H-benzo[f]cinnolin-2-one (1.05 g, 4.61 mmol) in methylene chloride (3 mL) was cooled to 0° C. Boron tribromide (23 ml of a 1M sol. in methylene chloride) was added and the reaction warmed to ambient temperature for 4 h. Re-cooled to 0° C. and sat. NH4Cl sol. (23 mL) was added. The solvents were removed under vacuum and water was added. Solids were filtered off and washed with cold methanol to produce 587 mg (59%). Mp>300° C. MS m/z 215 (M+H).

Workup

  1. customThe solvents were removed under vacuum and water
  2. additionwas added
  3. filtrationSolids were filtered off
  4. washwashed with cold methanol
  5. customto produce 587 mg (59%)

Sources & evidence

ORD record
ord-02204820f34b4090a895996f84f8bfb7
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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