Salicylaldehyde → HCID 12797772, compound

HRID 1464436Notes

Reaction equation

HRID 1464436 reaction equation
[H-].[Na+].[CH:3](=[O:11])[C:4]1[C:5](=[CH:7][CH:8]=[CH:9][CH:10]=1)[OH:6].Cl[C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=1[N+:23]([O-:25])=[O:24]>CN(C)C=O>[CH:3]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[O:6][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=1[N+:23]([O-:25])=[O:24])=[O:11]

Participants

5

Reactant 3

HCID 6998SalicylaldehydeHCID 24758Sodium hydrideHCID 735797Methyl 4-chloro-3-nitrobenzoate

Product 1

HCID 12797772HCID 12797772, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
103 °C

Procedure

Sodium hydride (3.09 g) was added in portions to a stirred solution of salicylaldehyde (14.3 g) in N,N-dimethylformamide (180 mL) under nitrogen. To the resulting dark solution was added methyl 4-chloro-3-nitrobenzoate (23.0 g) and N,N-dimethylformamide (50 mL), and the reaction was heated at 103° C. for 2.75 hours. The reaction was evaporated under vacuum, and the resulting oily mixture was partitioned between chloroform and water. The layers were separated, and the chloroform layer was washed with 1 M NaOH, water, and brine, dried over magnesium sulfate, and evaporated under vacuum to a yellow solid. Recrystalization from methanol yielded the title compound as light yellow crystals Mp: 109°-110° C.

Workup

  1. customThe reaction was evaporated under vacuum
  2. customthe resulting oily mixture was partitioned between chloroform and water
  3. customThe layers were separated
  4. washthe chloroform layer was washed with 1 M NaOH, water, and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under vacuum to a yellow solid
  7. customRecrystalization from methanol

Sources & evidence

ORD record
ord-e5b8f03eed8147fe813c69916dd006b3
Source dataset
uspto-grants-1994_04
Patent number
US05304644

Reaction notes

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