Sodium Hydroxide → 5-Nitro-2-thiophenecarboxaldehyde oxime

HRID 1860268Notes

Reaction equation

HRID 1860268 reaction equation
[N+:1]([C:4]1[S:8][C:7]([CH:9]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[NH2:12][OH:13].[OH-].[Na+]>C(O)C.O.ClCCl>[N+:1]([C:4]1[S:8][C:7]([CH:9]=[N:12][OH:13])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 782815-Nitrothiophene-2-carboxaldehydeHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 3505165-Nitro-2-thiophenecarboxaldehyde oximeYield 79.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 19096565Water ethanolSolvent

Procedure

A mixture of 5-nitrothiophene-2-carboxaldehyde (10 g, 64 mmol), hydroxylamine hydrochloride (9.4 g, 130 mmol) and sodium hydroxide (4.34 g, 107 mmol) in ethanol/water (150 ml, 2:1) was heated to reflux for 2 hours, then diluted with dichloromethane and washed with water. The organic layer was dried over magnesium sulfate and evaporated to dryness to give 8.8 g of 5-nitro-2-thiophene-carboxaldehyde oxime as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ: 7.54 (1H, d), 8.13 (1H, s), 8.16 (1H, d), 13.14 (1H, s).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. washwashed with water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-1b980d0a384e46658c2dd869af003b5c
Source dataset
uspto-grants-2003_03
Patent number
US06528653B2

Reaction notes

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