Nitroethane → 1-(2-Methoxy-6,7,8,9-tetrahydro-pyrido[1,2-a]indol-10-yl)-2-nitro-1-propene

HRID 2303959Notes

Reaction equation

HRID 2303959 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH2:12][CH2:13][CH2:14][CH2:15][C:7]1=[C:6]2[CH:16]=O.C([O-])(=O)C.[NH4+].[N+:23]([CH2:26][CH3:27])([O-:25])=[O:24]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH2:12][CH2:13][CH2:14][CH2:15][C:7]1=[C:6]2[CH:16]=[C:26]([N+:23]([O-:25])=[O:24])[CH3:27]

Participants

4

Reactant 3

HCID 6587NitroethaneHCID 517165Ammonium AcetateHCID 184620802-Methoxy-6,7,8,9-tetrahydro-pyrido[1,2-a]indole-10-carboxaldehyde

Product 1

HCID 698506431-(2-Methoxy-6,7,8,9-tetrahydro-pyrido[1,2-a]indol-10-yl)-2-nitro-1-propene

Procedure

A stirred solution of 2-methoxy-6,7,8,9-tetrahydro-pyrido[1,2-a]indole-10-carboxaldehyde and ammonium acetate in nitroethane is heated to 100° C. for 1 h, cooled to room temperature and partitioned between ethyl acetate and water. The combined organic extracts are washed (water, brine), dried (sodium sulfate) and concentrated in vacuo to give the product.

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe combined organic extracts are washed (water, brine)
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated in vacuo
  5. customto give the product

Sources & evidence

ORD record
ord-12b86162024f4182afcce83a0e8d7e35
Source dataset
uspto-grants-2002_08
Patent number
US06433175B1

Reaction notes

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