Sulfuric Acid → 1-[(3,4-Dihydro-2-naphthalenyl)methyl]-4-anilino isonipecotamide

HRID 2072484Notes

Reaction equation

HRID 2072484 reaction equation
O[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH:3]1[CH2:12][N:13]1[CH2:20][CH2:19][C:16]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:17]#[N:18])[CH2:15][CH2:14]1.S(=O)(=O)(O)[OH:29].[OH-].[NH4+]>>[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]=1[CH2:12][N:13]1[CH2:14][CH2:15][C:16]([NH:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)([C:17]([NH2:18])=[O:29])[CH2:19][CH2:20]1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 543671651-[(1,2,3,4-Tetrahydro-1-hydroxy-2-naphthalenyl)methyl]-4-anilino isonipecotonitrile

Product 1

HCID 214082231-[(3,4-Dihydro-2-naphthalenyl)methyl]-4-anilino isonipecotamide

Conditions

Temperature
70 °C

Procedure

A mixture of 1-[(1,2,3,4-tetrahydro-1-hydroxy-2-naphthalenyl)-methyl]-4-anilino isonipecotonitrile (5.0 g) and 90% sulfuric acid (60.0 g) is heated for 10 minutes at 70° C. The mixture is then stirred at room temperature for an additional hour. The reaction mixture is poured into ice-water, basified with ammonium hydroxide, and extracted with chloroform. Concentration of the dried chloroform solution followed by trituration with benzene yields the title compound.

Workup

  1. extractionextracted with chloroform

Sources & evidence

ORD record
ord-2ae114cd6fcf489ea27716a49e175767
Source dataset
uspto-grants-1977_09
Patent number
US04051248

Reaction notes

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