Hydrochloric Acid → 3-(2,3-dihydrobenzofur-7-yl)-3-methylbutanoic acid N,O-dimethylhydroxylamide

HRID 916045Notes

Reaction equation

HRID 916045 reaction equation
[O:1]1[C:5]2[C:6]([C:10]([CH3:16])([CH3:15])[CH2:11][C:12]([OH:14])=O)=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.O=S(Cl)Cl.Cl.[CH3:22][NH:23][O:24][CH3:25].Cl>C(Cl)Cl.N1C=CC=CC=1>[CH3:22][N:23]([O:24][CH3:25])[C:12](=[O:14])[CH2:11][C:10]([C:6]1[C:5]2[O:1][CH2:2][CH2:3][C:4]=2[CH:9]=[CH:8][CH:7]=1)([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 589600353-(2,3-Dihydro-1-benzofuran-7-yl)-3-methylbutanoic acid

Product 1

HCID 589600233-(2,3-dihydrobenzofur-7-yl)-3-methylbutanoic acid N,O-dimethylhydroxylamideYield 99.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

3-(2,3-Dihydrobenzofur-7-yl)-3-methylbutanoic acid (800 mg) in CH2Cl2 (10 mL) was treated with SOCl2 (0.315 mL) at 0° C. After 30 minutes, N,O-dimethylhydroxylamine hydrochloride (421 mg) in pyridine (1.5 mL) was added to the green mixture at 0° C. After another 30 minutes, 15 mL of 2 M HCl was added. The organic phase was separated and the aqueous layer was extracted with three 20 mL portions of CH2Cl2. The combined organic phases were dried over magnesium sulfate. The solvent was removed to yield 950 mg (99%) of 3-(2,3-dihydrobenzofur-7-yl)-3-methylbutanoic acid N,O-dimethylhydroxylamide as a yellowish oil.

Workup

  1. waitAfter another 30 minutes
  2. customThe organic phase was separated
  3. extractionthe aqueous layer was extracted with three 20 mL portions of CH2Cl2
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-cecd314799f345cf80f309d38f2e7735
Source dataset
uspto-grants-2007_09
Patent number
US07268152B2

Reaction notes

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