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

HRID 2072473Notes

Reaction equation

HRID 2072473 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[CH2:19][CH2:18][C:15]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:16]#[N:17])[CH2:14][CH2:13]1.S(=O)(=O)(O)[OH:28].[OH-].[NH4+]>>[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[CH2:19][CH2:18][C:15]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:16]([NH2:17])=[O:28])[CH2:14][CH2:13]1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 537070301-[(3,4-Dihydro-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-[(3,4-dihydro-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-5252351b68534317b9ddf53e3f6ec849
Source dataset
uspto-grants-1977_09
Patent number
US04051248

Reaction notes

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