Boron tribromide → HCID 22312843, compound

HRID 965611Notes

Reaction equation

HRID 965611 reaction equation
C[O:2][C:3]1[CH:20]=[CH:19][C:6]([NH:7][C:8]2[CH:18]=[CH:17][C:11]3[NH:12][C:13](=[O:16])[CH2:14][O:15][C:10]=3[CH:9]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:20]=[CH:19][C:6]([NH:7][C:8]2[CH:18]=[CH:17][C:11]3[NH:12][C:13](=[O:16])[CH2:14][O:15][C:10]=3[CH:9]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22312840HCID 22312840, compound

Product 1

HCID 22312843HCID 22312843, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7-(4-methoxyanilino)-2H-1,4-benzoxazin-3(4H)-one (135 mg; 0.5 mmol) in CH2Cl2 (2 ml) was treated with BBr3 (350 mg; 1.5 mmol). The mixture was stirred at room temperature for overnight. After evaporation to dryness the residue was taken up in EtOAC and saturated aqueous NaHCO3. The organic phase was washed with water, brine and dried over MgSO4. The residue (147 mg) was triturated with EtOAc, filtered and dried to give 7-(4-hydroxyanilino)-2H-1,4-benzoxazin-3-(4H)-one as a magenta solid (120 mg), Melting point 270-275° C. Yield: 94% 1H NMR spectrum (DMSO d6): 4.48(s, 2H); 6.46 (d, 1H); 6.48 (dd, 1H); 6.68-6.72 (m, 3H); 6.89 (m, 2H); 7.56 (s, 1H); 8.98 (s, 1H); 10.42 (s, 1H). LCMS-ESI: 256 [MH]+

Workup

  1. customAfter evaporation to dryness the residue
  2. washThe organic phase was washed with water, brine
  3. dry with materialdried over MgSO4
  4. customThe residue (147 mg) was triturated with EtOAc
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-18bb539bb65e4290a22b752d96edd281
Source dataset
uspto-grants-2005_10
Patent number
US06951855B2

Reaction notes

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