Water → HCID 59971430, compound

HRID 382009Notes

Reaction equation

HRID 382009 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][C:5](=[O:11])[NH:6]2.[NH:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[CH:17]=O.O>N1CCCCC1.CC(O)C>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1/[C:4](=[CH:17]/[C:13]1[NH:12][CH:16]=[CH:15][CH:14]=1)/[C:5](=[O:11])[NH:6]2

Participants

6

Reactant 3

HCID 962WaterHCID 13854Pyrrole-2-carboxaldehydeHCID 27631904-bromo-2,3-dihydro-1H-indol-2-one

Product 1

HCID 59971430HCID 59971430, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8082PiperidineSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4-bromo-1,3-dihydro-2H-indol-2-one (0.2 g, 0.94 mmol) (see Kosuge et al., supra), and excess pyrrole-2-carboxaldehyde (0.11 g, 1.13 mmol) (Aldrich) in 1% piperidine in 2-propanol (2 mL) was heated at 85° C. for 2 h. Hot water (2 mL) was added. On cooling, the crystallized product was filtered off, washed with aqueous 2-propanol and dried. (Yield 0.26 g, 96%).

Workup

  1. temperatureOn cooling
  2. filtrationthe crystallized product was filtered off
  3. washwashed with aqueous 2-propanol
  4. customdried

Sources & evidence

ORD record
ord-fb8c200ef8b14006b47ac1d51ac9f564
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Reaction notes

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