4-Iodoaniline → HCID 178501771, compound

HRID 1176077Notes

Reaction equation

HRID 1176077 reaction equation
[CH:1]([C:3]1[CH:14]=[CH:13][C:6]([O:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1)=O.[I:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[I:15][C:16]1[CH:22]=[CH:21][C:19](/[N:20]=[CH:1]/[C:3]2[CH:14]=[CH:13][C:6]([O:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 108934-IodoanilineHCID 758214Methyl 2-(4-formylphenoxy)acetate

Product 1

HCID 178501771HCID 178501771, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl (4-formylphenoxy)acetate (8.0 g, 40 mmol) was dissolved in 100 ml toluene and p-iodoaniline (9.1 g, 40 mmol) was added. The mixture was refluxed over night using a Dean-Stark apparatus. The reaction mixture was partly evaporated under reduced pressure. Methanol was added to the suspension and the mixture was stirred for a few minutes. The precipitate was filtered off, washed with methanol and dried under reduced pressure over night to yield the title compound. 1H-NMR (400 MHz, CDCl3) δ: 3.83 (s, 3H), 4.72 (s, 2H), 6.95 (d, 2H), 7.00 (d, 2H), 7.69 (d, 2H), 7.86 (d, 2H), 8.35 (s, 1H).

Workup

  1. temperatureThe mixture was refluxed over night
  2. customThe reaction mixture was partly evaporated under reduced pressure
  3. additionMethanol was added to the suspension
  4. filtrationThe precipitate was filtered off
  5. washwashed with methanol
  6. customdried under reduced pressure over night

Sources & evidence

ORD record
ord-12f03b0399924fb8bbfc17e62c80c9a0
Source dataset
uspto-grants-2010_11
Patent number
US07842684B2

Reaction notes

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