Potassium Carbonate → 5-Bromo-6-methoxybenzo[d]isoxazol-3-ylamine

HRID 2396726Notes

Reaction equation

HRID 2396726 reaction equation
[NH2:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:5]=2[O:4][N:3]=1.[Br:13]Br.C([O-])([O-])=O.[K+].[K+].[O-]S([O-])=O.[Na+].[Na+]>CO.CC(C)=O.C(Cl)(Cl)Cl>[NH2:1][C:2]1[C:6]2[CH:7]=[C:8]([Br:13])[C:9]([O:11][CH3:12])=[CH:10][C:5]=2[O:4][N:3]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 24408Bromine2×HCID 24437Sodium SulfiteHCID 106785796-Methoxy-1,2-benzoxazol-3-amine

Product 1

HCID 187964575-Bromo-6-methoxybenzo[d]isoxazol-3-ylamineYield 67.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 15930782Chloroform acetoneSolvent

Procedure

To a stirred solution of 3-amino-6-methoxy-1,2-benzisoxazole (14 g) in methanol (1 L) was added a solution of bromine (13.6 g) and methanol (200 ml) dropwise at -50° C. under N2. The mixture was allowed to warm to room temperature after the addition was complete. After 24 hours an additional 1/4 equivalent of bromine was added. TLC (10% acetone/CHCl3) showed no starting material 24 hours later. The reaction was neutralized with saturated K2CO3 solution, treated with saturated Na2SO3 solution triturated with water, filtered, and washed with water. The crude product was dried in vacuo affording 14 g of product, m.p. 226°-227° C.

Workup

  1. additionafter the addition
  2. customno starting material 24 hours
  3. customtriturated with water
  4. filtrationfiltered
  5. washwashed with water
  6. dry with materialThe crude product was dried in vacuo

Sources & evidence

ORD record
ord-c5b55bef8ab349fc9ad59fb32009f32e
Source dataset
uspto-grants-1996_02
Patent number
US05494908

Reaction notes

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