Acetic Anhydride → HCID 45096723, compound

HRID 2375302

Reaction equation

HRID 2375302 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]=O)=[CH:8][C:7]([N+:13]([O-:15])=[O:14])=[CH:6][CH:5]=2.Cl.[NH2:17]O.C(OC(=O)C)(=O)C>C(O)=O.CN(C=O)C.O>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]#[N:17])=[CH:8][C:7]([N+:13]([O-:15])=[O:14])=[CH:6][CH:5]=2

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 443297Hydroxyamine hydrochlorideHCID 6093592-methyl-5-nitro-1H-indole-3-carbaldehyde

Product 1

HCID 45096723HCID 45096723, compoundYield 89.1%

Reagents, catalysts & solvents 3

HCID 284Formic AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-methyl-5-nitro-1H-indole-3-carbaldehyde (375 mg, 1.84 mmol) and hydroxylamine hydrochloride (380 mg, 5.52 mmol) were suspended in formic acid (10 mL) and DMF (3 mL), and heated at 80° C. until the solution had turned dark orange (30 min). Quantitative conversion to the aldoxime intermediate was confirmed by LC/MS. 4 mL of acetic anhydride were added and heating was continued for 1 h. The reaction solution was diluted with cold water (20 mL), and the product extracted into EtOAc. The organic layer was washed with water (2×50 mL), brine (2×50 mL), dried over MgSO4, and filtered. The solvent was removed in vacuo to yield 2-methyl-5-nitro-1H-indole-3-carbonitrile as an ochre-colored solid (330 mg, 89% yield). Mass and purity were confirmed by LC/MS using an acetonitrile gradient with 0.035% TFA/water. Theoretical (M+H)+ m/z for C10H7N3O2=202.05; Found 202.2.

Workup

  1. customorange (30 min)
  2. temperatureheating
  3. extractionthe product extracted into EtOAc
  4. washThe organic layer was washed with water (2×50 mL), brine (2×50 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-6eefa4990f134a02a1edc0b81a13b8da
Source dataset
uspto-grants-2008_12
Patent number
US07465738B2

Linked notes

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