Acetohydroxamic Acid → 3-Amino-6-methoxymethoxy-1,2-benzisoxazole

HRID 1003338Notes

Reaction equation

HRID 1003338 reaction equation
CC(C)([O-])C.[K+].F[C:8]1[CH:15]=[C:14]([O:16][CH2:17][O:18][CH3:19])[CH:13]=[CH:12][C:9]=1[C:10]#[N:11].C([NH:23][OH:24])(=O)C>CN(C)C=O.CC(C)=O.C(Cl)(Cl)Cl.CCOC(C)=O>[NH2:11][C:10]1[C:9]2[CH:12]=[CH:13][C:14]([O:16][CH2:17][O:18][CH3:19])=[CH:15][C:8]=2[O:24][N:23]=1

Participants

8

Reactant 4

HCID 1990Acetohydroxamic AcidHCID 109541382-Fluoro-4-(methoxymethoxy)-benzonitrileHCID 23665647Potassium tert-butoxideHCID 178418922HCID 178418922, compound

Product 1

HCID 110087953-Amino-6-methoxymethoxy-1,2-benzisoxazole

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolventHCID 15930782Chloroform acetoneSolvent

Procedure

To a stirred solution of acetophydroxamic acid (3.88 g) in N,N-dimethylformamide (DMF) (120 ml) was added potassium tertiarybutoxide (tBuOK) (5.80 g) under N2. After one hour of stirring 2-fluoro-4-(methoxymethoxy)-benzonitrile (6.0 g) was added. Stirring continued for 16 hours. TLC (silica gel) in 10% acetone/CHCl3 showed the presence of starting material. An additional 1 equivalent of acetohydroxamic acid and tBuOK were added in DMF (120 ml). After one hour the reaction was diluted with EtOAc (2 l), filtered, washed filtrate with brine (4×11), dried (MgSO4), and concentrated in vacuo. Flash column chromatography (silica gel) was performed eluting with 2.5% acetone/CH2Cl2 solution affording 8.1 g of the product, m.p. 88-89° C.

Workup

  1. filtrationfiltered
  2. washwashed filtrate with brine (4×11)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. washFlash column chromatography (silica gel) was performed eluting with 2.5% acetone/CH2Cl2 solution

Sources & evidence

ORD record
ord-d7606d1b914349f8a9a0db6753e48907
Source dataset
uspto-grants-2000_04
Patent number
US06046203

Reaction notes

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