Water → HCID 69662484, compound

HRID 1743804Notes

Reaction equation

HRID 1743804 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][C:7]3[O:11][CH2:12][CH2:13][CH2:14][C:6]=3[C:5]=2[C:4]([CH:15]=O)=[CH:3]1.C([O-])(=O)C.[NH4+].O.[N+:23]([CH2:26][CH3:27])([O-:25])=[O:24]>>[N+:23]([C:26]([CH3:27])=[CH:15][C:4]1[C:5]2[C:6]3[CH2:14][CH2:13][CH2:12][O:11][C:7]=3[CH:8]=[CH:9][C:10]=2[N:2]([CH3:1])[CH:3]=1)([O-:25])=[O:24]

Participants

5

Reactant 4

HCID 962WaterHCID 6587NitroethaneHCID 517165Ammonium AcetateHCID 10013517HCID 10013517, compound

Product 1

HCID 69662484HCID 69662484, compoundYield 85%

Conditions

Temperature
100 °C

Procedure

A mixture of 3-methyl-3,7,8,9-tetrahydro-pyrano[3,2-e]indole-1-carboxaldehyde (1.02 g, 4.74 mmol) and ammonium acetate (0.30 g, 3.90 mmol) in 12 ml of nitroethane was heated at 100° C. for 3 h, stirred at room temperature for 18 h, mixed with water (50 ml) and extracted with EtOAc (3×50 ml). The combined extracts were dried (MgSO4), filtered and evaporated to dryness. Crystallization of the residue from a mixture of dichloromethane and hexane gave an orange solid (1.10 g, 85%): mp 200-202° C.

Workup

  1. extractionextracted with EtOAc (3×50 ml)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customCrystallization of the residue
  6. additionfrom a mixture of dichloromethane and hexane

Sources & evidence

ORD record
ord-1461c142e98a442786427776ff7fc778
Source dataset
uspto-grants-2006_03
Patent number
US07012090B1

Reaction notes

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