Ethanol → HCID 117601757, compound

HRID 1773668Notes

Reaction equation

HRID 1773668 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:14]=[C:13]([N+:15]([O-])=O)[C:10]([NH:11][CH3:12])=[C:9]([I:18])[CH:8]=2)=[C:5]([CH3:19])[O:4][N:3]=1.CCO.[Sn](Cl)Cl>[OH-].[Na+]>[CH3:1][C:2]1[C:6]([C:7]2[CH:14]=[C:13]([NH2:15])[C:10]([NH:11][CH3:12])=[C:9]([I:18])[CH:8]=2)=[C:5]([CH3:19])[O:4][N:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24479Stannous ChlorideHCID 117601702HCID 117601702, compound

Product 1

HCID 117601757HCID 117601757, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
110 °C

Procedure

Into a microwave vial containing 4-(3,5-dimethylisoxazol-4-yl)-2-iodo-N-methyl-6-nitroaniline (610 mg, 1.64 mmol, 1 equiv) is added EtOH (12 mL, 0.25M) and tin (II) chloride (622 mg, 3.28 mmol, 2 equiv). The reaction was heated for 30 min at 110° C. The reaction was then stirred in 2N NaOH solution for 20 minutes before being partitioned between water and ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. Purification was carried out by flash column chromatography to furnish 4-(3,5-dimethylisoxazol-4-yl)-6-iodo-N1-methylbenzene-1,2-diamine.

Workup

  1. custombefore being partitioned between water and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customPurification

Sources & evidence

ORD record
ord-64ca83dd756a44bba18412d144fac7ff
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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