3-Hydroxybenzaldehyde → HCID 87611787, compound

HRID 1166196Notes

Reaction equation

HRID 1166196 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].C(N(CC)CC)C.[CH3:17][C:18]1[N:26]([C:27]([C:29]2[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=2)=[O:28])[C:25]2[CH:24]=[CH:23][C:22]([O:36][CH3:37])=[CH:21][C:20]=2[C:19]=1[CH2:38][C:39](O)=[O:40].O>C(Cl)Cl>[CH:5]([C:4]1[CH:3]=[C:2]([O:1][C:39](=[O:40])[CH2:38][C:19]2[C:20]3[C:25](=[CH:24][CH:23]=[C:22]([O:36][CH3:37])[CH:21]=3)[N:26]([C:27](=[O:28])[C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[C:18]=2[CH3:17])[CH:9]=[CH:8][CH:7]=1)=[O:6]

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 962WaterHCID 3715IndomethacinHCID 8471Triethylamine

Product 1

HCID 87611787HCID 87611787, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-hydroxybenzaldehyde (g 8.30) and triethylamine (g 0.824) in methylene chloride (200 ml), cooling at a temperature in the range −5° C.-0° C. indomethacin in the form of the corresponding acylchloride (g 16.50) is added under stirring. It is still maintained under stirring for 15 minutes, then water (100 ml) is added and the phases are separated. The aqueous phase is recovered and extracted with methylene chloride (300 ml). The organic phases are joined together, washed with a 5% Na2CO3 solution, the organic phase is anhydrified with sodium sulphate obtaining the expected compound.

Workup

  1. additionis added
  2. temperatureIt is still maintained
  3. stirringunder stirring for 15 minutes
  4. customthe phases are separated
  5. customThe aqueous phase is recovered
  6. extractionextracted with methylene chloride (300 ml)
  7. washwashed with a 5% Na2CO3 solution

Sources & evidence

ORD record
ord-b1543a2dec604cf480e65d22252d4c52
Source dataset
uspto-grants-2003_09
Patent number
US06613784B1

Reaction notes

Loading…