Toluene → HCID 178517902, compound

HRID 2072474Notes

Reaction equation

HRID 2072474 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]=1[CH2:11][N:12]1[CH2:20][CH2:19][C:15]([NH:21][C:22]2C=CC=CC=2)([C:16]([NH2:18])=[O:17])[CH2:14][CH2:13]1.C(OCC)(OCC)OCC.C1(C)C=CC=CC=1.[OH-].[NH4+]>C(O)(=O)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]=1[CH2:11][N:12]1[CH2:13][CH2:14][C:15]2([NH:21][CH:22]=[N:18][C:16]2=[O:17])[CH2:19][CH2:20]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 14923Ammonium HydroxideHCID 31214Ethyl orthoformateHCID 214082231-[(3,4-Dihydro-2-naphthalenyl)methyl]-4-anilino isonipecotamide

Product 1

HCID 178517902HCID 178517902, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1-[(3,4-dihydro-2-naphthalenyl)methyl]-4-anilino isonipecotamide (6.0 g), triethyl orthoformate (3.0 g), toluene (30 ml), and glacial acetic acid (1.5 ml) is refluxed under nitrogen for 38 hours. The reaction mixture is cooled and poured into aqueous ammonium hydroxide. The organic layer is separated, dried, and concentrated to give the crude product. Digestion of this material with benzene followed by filtration and concentration of the organic solution yields the title compound.

Workup

  1. temperatureis refluxed under nitrogen for 38 hours
  2. temperatureThe reaction mixture is cooled
  3. customThe organic layer is separated
  4. customdried
  5. concentrationconcentrated
  6. customto give the crude product
  7. filtrationDigestion of this material with benzene followed by filtration and concentration of the organic solution

Sources & evidence

ORD record
ord-ef88f300af0b4791a2a6a5332dce9a59
Source dataset
uspto-grants-1977_09
Patent number
US04051248

Reaction notes

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