Ethanol → HCID 117601757, compound

HRID 1773713Notes

Reaction equation

HRID 1773713 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

To a microwave vial containing 4-(3,5-dimethylisoxazol-4-yl)-2-iodo-N-methyl-6-nitroaniline (610 mg, 1.64 mmol, 1 equiv) was added EtOH (12 mL, 0.25M) and tin (II) chloride (622 mg, 3.28 mmol, 2 equiv). The reaction mixture was heated for 30 min at 110° C. The reaction was then stirred in 2N NaOH solution for 20 minutes and 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. custompartitioned 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-3af1a6de6446419a9cd2d0edd6e2a41b
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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