1-Chloro-2,4-Dinitrobenzene → 2-Amino-4-Nitrophenol

HRID 1065537

반응식

HRID 1065537 반응식
[N+](C1C=C([N+]([O-])=O)C=CC=1Cl)([O-])=O.[N+:14]([C:17]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=1[O-:26])([O-])=O.[Na+].[Cl-].[NH4+].NC1C=C([N+]([O-])=O)C=CC=1[O-].[Na+].[SH-]>O>[NH2:14][C:17]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=1[OH:26]

참가 물질

7

반응물 5

HCID 61-Chloro-2,4-DinitrobenzeneHCID 25517Ammonium ChlorideHCID 70533Sodium 2,4-dinitrophenolateHCID 5047209Hydrosulfide2회HCID 5485279Sodium 2-amino-4-nitrophenoxide

생성물 1

HCID 36133892-Amino-4-Nitrophenol

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
15 °C

실험 절차

202.6 parts of 2,4-dinitrochlorobenzene are converted into sodium 2,4-dinitrophenolate in accordance with the statements in Example 1 and, after adding 400 parts of water and 184 parts of ammonium chloride, the pH value is adjusted to 7.0. Reduction to sodium 2-amino-4-nitrophenolate is carried out with 580 parts of 31.9% strength hydrosulphide solution at pH values of at most 9, whilst stirring and monitoring the pH. After addition of the hydrosulphide, the mixture is subsequently stirred at 70° to 75° C. for about 45 minutes and the sulphur which has precipitated is filtered off. 100 g of sodium sulphite are added to the filtrate and the mixture is cooled to about 15° C. and adjusted to a pH of 5.6 to 5.8 with 136 parts of 30% strength hydrochloric acid. The mixture is subsequently stirred for about a further hour at 5° to 10° C. and filtered and the filter cake is rinsed with about 200 parts of 26% strength aqueous sodium chloride solution. 277.6 parts of a 53.3% strength aqueous press cake of 2-amino-4-nitrophenol, corresponding to 147.9 parts of 100% pure 2-amino-4-nitrophenol (96% of theory, relative to 2,4-dinitrochlorobenzene) are obtained. The product has a sulphur content of <0.1% and a melting point of 144° C.

후처리

  1. stirringthe mixture is subsequently stirred at 70° to 75° C. for about 45 minutes
  2. customthe sulphur which has precipitated
  3. filtrationis filtered off
  4. addition100 g of sodium sulphite are added to the filtrate
  5. stirringThe mixture is subsequently stirred for about a further hour at 5° to 10° C.
  6. filtrationfiltered
  7. washthe filter cake is rinsed with about 200 parts of 26% strength aqueous sodium chloride solution

출처 및 근거

ORD 기록
ord-47fe57e24fb0482382ac022f959c4a27
출처 데이터셋
uspto-grants-1982_05
특허 번호
US04329503

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