Methanol → HCID 23025926, compound

HRID 1437479Notes

Reaction equation

HRID 1437479 reaction equation
[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]=[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-])=O)[CH:10]=3)[O:8][C:4]=2[CH:3]=1.CO.[BH4-].[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1>[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]=[C:7]([C:9]3[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=3)[NH2:15])[O:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 23025951HCID 23025951, compound

Product 1

HCID 23025926HCID 23025926, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 6-bromo-2-(3-nitrophenyl)benzoxazole (Compound of Example 266) (5.96 g), nickel bromide(II) (204 mg), methanol (100 ml), tetrahydrofuran (100 ml) was added sodium borohydride (2.12 g) little by little at 0° C. The mixture was stirred at 0° C. for 10 minutes and at room temperature for 1 hour. The reaction mixture was poured into a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The organic layer was washed with water, dried over MgSO4 and treated with activated carbon. The solvent was distilled off under reduced pressure, and resulting crystals were collected by filtration to obtain 3-(6-bromobenzoxazol-2-yl)aniline (4.46 g, 83%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over MgSO4
  4. additiontreated with activated carbon
  5. distillationThe solvent was distilled off under reduced pressure
  6. customresulting crystals
  7. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-6ea185d638d447eea7219b008ac82aaa
Source dataset
uspto-grants-2009_11
Patent number
US07622479B2

Reaction notes

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