4-Aminophenol → HCID 18368265, compound

HRID 379702Notes

Reaction equation

HRID 379702 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=O)[CH2:3][CH2:2]1.C(C1NC=CN=1)(C1NC=CN=1)=O.[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1>>[OH:29][C:26]1[CH:27]=[CH:28][C:23]([NH:22][C:7]([CH:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)=[O:9])=[CH:24][CH:25]=1

Participants

4

Reactant 3

HCID 4034-AminophenolHCID 219302Oxane-4-carboxylic acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 1

HCID 18368265HCID 18368265, compoundYield 79.4%

Procedure

3,4,5,6-Tetrahydro-2H-pyran-4-carboxylic acid (10.0 g) solution in dimethylformamido (15 ml) was added drop-wise with carbonyl diimidazole (13.1 g) in dimethylformamido (65 ml) in an ice bath and the mixture was stirred for 30 minutes at room temperature. 4-Aminophenol (8.4 g) solution in dimethylformamido (20 ml) was added drop-wise to this mixture in ice bath and the mixture was stirred for 5 hours at room temperature. The reaction mixture was concentrated to small volume and further stirred after addition of 2N HCl (100 ml). Crystals formed were collected by filtration, washed with water and then dried under vacuum at 60° C. to obtain 4′-hydroxy-3,4,5,6-tetrahydro-2H-pyran-4-carboxanilide (13.5 g) as white crystal.

Workup

  1. stirringthe mixture was stirred for 5 hours at room temperature
  2. concentrationThe reaction mixture was concentrated to small volume
  3. stirringfurther stirred
  4. additionafter addition of 2N HCl (100 ml)
  5. customCrystals formed
  6. filtrationwere collected by filtration
  7. washwashed with water
  8. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-77e2118552274946abd3289cde946c60
Source dataset
uspto-grants-2001_10
Patent number
US06300368B1

Reaction notes

Loading…