Pyridine → HCID 22287130, compound

HRID 2301057Notes

Reaction equation

HRID 2301057 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH2:4].N1C=CC=C[CH:11]=1.[C:16]([O:19][C:20]([CH3:25])(C)[C:21](Cl)=[O:22])(=[O:18])[CH3:17]>C(Cl)Cl>[Cl:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH:4][C:21](=[O:22])[CH:20]([O:19][C:16](=[O:18])[CH3:17])[CH2:25][CH3:11]

Participants

5

Reactant 3

HCID 1049PyridineHCID 1234962-Acetoxyisobutyroyl chlorideHCID 2829302-Chloro-4-iodoaniline

Product 1

HCID 22287130HCID 22287130, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

2-Chloro-4-iodoaniline (5 g) was dissolved in DCM (100 ml) and cooled to 0-5° C. in an ice bath. Pyridine (2.1 ml) was added followed by dropwise addition of 2-acetoxy-2-methylpropanoyl chloride (3.44 ml) and the mixture was allowed to warm to ambient temperature over 15 hours. The solvent was removed by evaporation and the residue was purified by flash chromatography eluting with 10-50% ethyl acetate/hexane to give the title compound (7.5 g) as a solid. Mp 156-158° C.; NMR (CDCl3): 1.7 (s. 6H), 2.2 (s, 3H), 7.6 (d, 1H), 7.7 (d, 1H), 8.2 (d, 1H), 8.4 (s, 1H); MS (ESP−): 380.

Workup

  1. temperatureto warm to ambient temperature over 15 hours
  2. customThe solvent was removed by evaporation
  3. customthe residue was purified by flash chromatography
  4. washeluting with 10-50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-85a3f8044bc04993bfbafcd3b529f208
Source dataset
uspto-grants-2002_12
Patent number
US06498275B1

Reaction notes

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