1-Chloro-2,4-Dinitrobenzene → HCID 20267379, compound

HRID 1719642Notes

Reaction equation

HRID 1719642 reaction equation
[N+](C1C=C([N+]([O-])=O)C=CC=1[Cl:13])([O-])=O.[OH-].[Na+].[CH2:16]([O:20][C:21]1[C:26]([NH2:27])=[CH:25][C:24]([NH:28][C:29](=[O:31])[CH3:30])=[CH:23][CH:22]=1)[CH2:17][CH2:18][CH3:19].C(NC1C=C(NC(=O)C)C=CC=1OCCCC)(=O)C.NC1C=C(N)C=CC=1OCCCC>C(O)CCC>[ClH:13].[CH2:16]([O:20][C:21]1[C:26]([NH2:27])=[CH:25][C:24]([NH:28][C:29](=[O:31])[CH3:30])=[CH:23][CH:22]=1)[CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 5

HCID 61-Chloro-2,4-DinitrobenzeneHCID 14798Sodium HydroxideHCID 1536951,3-Benzenediamine, 4-butoxy-HCID 20267376HCID 20267376, compoundHCID 57324858HCID 57324858, compound

Product 1

HCID 20267379HCID 20267379, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

The dark butanolic solution, obtained according to European Pat. No. 0,011,048 by reaction of 213 parts of 2,4-dinitrochlorobenzene with 632 parts of n-butanol and 42 parts of sodium hydroxide, after hydrogenation and acetylation, of 6-n-butoxy-3-acetylamino-aniline which, according to HPLC analysis, contains, in addition to 195 parts of target product, 11.9 parts of 2,4-bis-acetylamino-1-n-butoxy-benzene and 8.1 parts of 2,4-diamino-1-n-butoxybenzene, in addition to unknown decomposition products formed by oxidation, is precipitated by gassing with 35-40 parts of hydrogen chloride at 20°-30° C. for one hour and, after cooling to 0°-5° C., the precipitate is filtered off with suction, washed twice with 50 parts of methanol each time and dried in vacuo. 221.2 parts of 6-n-butoxy-3-acetylamino-aniline hydrochloride are obtained which, besides about 3% of magnesium chloride, contains no impurities at all which can be detected by HPLC analysis (purity by diazotization: 95.8%). This corresponds to a yield of 214.1 parts of 100% pure 6-n-butoxy-3-acetylamino-aniline hydrochloride (82.8% of theory, based on 2,4-dinitrochlorobenzene).

Workup

  1. customThe dark butanolic solution, obtained
  2. customformed by oxidation
  3. customis precipitated
  4. temperatureafter cooling to 0°-5° C.
  5. filtrationthe precipitate is filtered off with suction
  6. washwashed twice with 50 parts of methanol each time
  7. customdried in vacuo

Sources & evidence

ORD record
ord-25c9e8e3cca144dda621f023bcbb51c8
Source dataset
uspto-grants-1985_09
Patent number
US04540815

Reaction notes

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