Hydrochloric Acid → HCID 22464567, compound

HRID 325077Notes

Reaction equation

HRID 325077 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH3:12].Cl[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]Cl.Cl>ClC1C=CC=CC=1>[CH3:12][C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]=1[N:1]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9533Bis(2-chloroethyl)amineHCID 167332-Methyl-1-naphthylamine

Product 1

HCID 22464567HCID 22464567, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

13.0 g (82.7 mmol) of 1-amino-2-methylnaphthalene in 100 ml of chlorobenzene were mixed with 14.7 g (82.7 mmol) of bis(2-chloroethyl)amine×HCl and refluxed under nitrogen for 90 h. The mixture was then concentrated and partitioned between methylene chloride and water at pH=9, and the organic phase was dried and then concentrated. The crude product was purified by column chromatography (silica gel, mobile phase/THF/methanol/ammonia 85/13/2. 11.6 g (62%) of product were isolated.

Workup

  1. temperaturerefluxed under nitrogen for 90 h
  2. concentrationThe mixture was then concentrated
  3. custompartitioned between methylene chloride and water at pH=9
  4. customthe organic phase was dried
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (silica gel, mobile phase/THF/methanol/ammonia 85/13/2

Sources & evidence

ORD record
ord-73f50edd0e62415c95bf3b24e07190c1
Source dataset
uspto-grants-2001_04
Patent number
US06222034B1

Reaction notes

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