5-Nitrosalicylaldehyde → Benzaldehyde, 2-hydroxy-5-nitro-, oxime

HRID 1916354Notes

Reaction equation

HRID 1916354 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=O.Cl.[NH2:14][OH:15]>N1C=CC=CC=1.CCO.C(Cl)Cl>[OH:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=[N:14][OH:15]

Participants

6

Reactant 2

HCID 668085-NitrosalicylaldehydeHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 3249955Benzaldehyde, 2-hydroxy-5-nitro-, oximeYield 81%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 2-hydroxy-5-nitrobenzaldehyde (2.10 g, 12.6 mmol) in pyridine (31.0 mL) and EtOH (5.0 mL) was added hydroxylamine hydrochloride (1.75 g, 25.2 mmol). After stirring at 20° C. for 10 h, the mixture was diluted with CH2Cl2 (125 mL) and washed with water (4×70 mL) and brine (50 mL). The organic layer was dried (Na2SO4) and evaporated. The residue was triturated with EtOH and filtered. The resulting solid was rinsed with ether and dried under vacuum to obtain the title compound (1.86 g, 81% yield) as a yellowish solid: MS (electrospray, +ions) m/z 183 (M+H).

Workup

  1. washwashed with water (4×70 mL) and brine (50 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customevaporated
  4. customThe residue was triturated with EtOH
  5. filtrationfiltered
  6. washThe resulting solid was rinsed with ether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-c48bf80674db443ea167899afa0e5c0b
Source dataset
uspto-grants-2013_12
Patent number
US08618115B2

Reaction notes

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