4-Iodoaniline → HCID 19908434, compound

HRID 1534864Notes

Reaction equation

HRID 1534864 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:17])([C:13]([O:15][CH3:16])=[O:14])[CH2:11][C:10]([C:18]([O:20]C)=O)=[N:9]2)=[CH:4][CH:3]=1.C[Al](C)C.[I:26][C:27]1[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=1>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([CH3:17])([C:13]([O:15][CH3:16])=[O:14])[CH2:11][C:10]([C:18]([NH:31][C:30]3[CH:32]=[CH:33][C:27]([I:26])=[CH:28][CH:29]=3)=[O:20])=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 108934-IodoanilineHCID 16682925TrimethylaluminumHCID 19908445HCID 19908445, compound

Product 1

HCID 19908434HCID 19908434, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The compound of Example 11 (0.5 g) was dissolved in dichloromethane (5 ml) and added to a mixture of trimethylaluminum (2M in toluene, 1.68 ml) and 4-iodoaniline (0.7 g) in dichloromethane (10 ml). The mixture was stirred at room temperature for 16 hours and partitioned between 1N HCl (100 ml) and dichloromethane (100 ml). The organic layer was dried and evaporated to leave a solid. Recrystallization from ether/hexanes gave the title compound (0.73 g): m.p.: 84°-85° C. NMR (CDCl3) 8.4 (br, NH), 7.7-6.9 (m, ArH, 12H), 3.8 (s, OMe, 3H), 3.8 (d, CH, 1H), 3.3 (d, CH, 1H), 1.7 (s, Me, 3H).

Workup

  1. custompartitioned between 1N HCl (100 ml) and dichloromethane (100 ml)
  2. customThe organic layer was dried
  3. customevaporated
  4. customto leave a solid
  5. customRecrystallization from ether/hexanes

Sources & evidence

ORD record
ord-19a7cb45db6244108bdde1bb46d13d9b
Source dataset
uspto-grants-1992_02
Patent number
US05091405

Reaction notes

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