Hydrochloric Acid → HCID 21420828, compound

HRID 441364Notes

Reaction equation

HRID 441364 reaction equation
C(O)C.Cl.[CH3:5][C:6]1[CH:21]=[CH:20][C:9]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[C:8]([N+:22]([O-])=O)[CH:7]=1.[OH-].[Na+]>[Fe].O>[CH3:5][C:6]1[CH:21]=[CH:20][C:9]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[C:8]([NH2:22])[CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 21420829HCID 21420829, compound

Product 1

HCID 21420828HCID 21420828, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A mixture of ethanol (1685 parts), water (210 parts), hydrochloric acid (density 1.18 g. ml.) (20 parts) and iron powder (820 parts) was stirred vigorously and boiled for 1 hour when an ethanolic (420 parts) solution of 4-methyl-2-nitro-N-nonylaniline (575 parts) was added during 30 minutes. The mixture was boiled for 15 hours when sodium hydroxide solution (density 1.35 g. ml.) (20 parts) were added and the mixture was filtered while still hot and the residue was washed with boiling ethanol. After removal of the solvent from the combined filtrate and washings the residual oil was distilled under reduced pressure to give 4-methyl-2-amino-N-nonylaniline (390 parts) as a pale yellow oil, boiling point 176° C. at 0.7 mm, which solidified on cooling.

Workup

  1. waitThe mixture was boiled for 15 hours
  2. filtrationthe mixture was filtered while still hot and the residue
  3. washwas washed with boiling ethanol
  4. customAfter removal of the solvent from the combined filtrate and washings the residual oil
  5. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-d149067cd96c4505b3c9b6088f616fe3
Source dataset
uspto-grants-1977_08
Patent number
US04039612

Reaction notes

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