HCID 54083854, compound → 2-Amino-5-iodo-3-methylbenzaldehyde

HRID 2231652Notes

Reaction equation

HRID 2231652 reaction equation
[NH2:1][C:2]1[C:9]([CH3:10])=[CH:8][C:7]([I:11])=[CH:6][C:3]=1[CH2:4][OH:5]>ClCCl.[O-2].[O-2].[Mn+4]>[NH2:1][C:2]1[C:9]([CH3:10])=[CH:8][C:7]([I:11])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

4

Reactant 1

HCID 54083854HCID 54083854, compound

Product 1

HCID 212855162-Amino-5-iodo-3-methylbenzaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Freshly dried manganese dioxide (3.3 g) was added to a solution of 2-amino-5-iodo-3-methylbenzyl alcohol (2.0 g) in dichloromethane (50 cm3) under nitrogen and the mixture was stirred for 3 days at room temperature. The mixture was filtered, the filtrate evaporated to dryness, and the solid residue was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with dichloromethane. Combination and evaporation of appropriate fractions afforded the title compound, m.p. 134° (1.6 g).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated to dryness
  3. customthe solid residue was chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  4. washeluting with dichloromethane
  5. customCombination and evaporation of appropriate fractions

Sources & evidence

ORD record
ord-38c2632cf9b04a5f82d1c7cf1b1481b1
Source dataset
uspto-grants-1988_11
Patent number
US04783467

Reaction notes

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