홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

1-Chloro-2,4-Dinitrobenzene → 6-Methoxy-3-acetylamino-aniline hydrochloride

HRID 1719639
노트
인쇄 미리보기

반응식

HRID 1719639 반응식
Cl.[N+](C1C=C([N+]([O-])=O)C=CC=1[Cl:14])([O-])=O.[OH-].[Na+].C(OC(=O)C)(=O)C.[O-2].[Mg+2].[CH3:26][O:27][C:28]1[C:33]([NH2:34])=[CH:32][C:31]([NH:35][C:36](=[O:38])[CH3:37])=[CH:30][CH:29]=1.C(NC1C=C(NC(=O)C)C=CC=1OC)(=O)C.NC1C=C(N)C=CC=1OC>CO>[ClH:14].[CH3:26][O:27][C:28]1[C:33]([NH2:34])=[CH:32][C:31]([NH:35][C:36](=[O:38])[CH3:37])=[CH:30][CH:29]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

10

반응물 8

HCID 61-Chloro-2,4-DinitrobenzeneHCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 119762,4-DiaminoanisoleHCID 14798Sodium HydroxideHCID 807793'-Amino-4'-methoxyacetanilideHCID 153420Acetamide, N,N'-(4-methoxy-1,3-phenylene)bis-
HCID 6850729
Magnesium monoxide

생성물 1

HCID 202673776-Methoxy-3-acetylamino-aniline hydrochloride수율 100%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

197 parts of 37% strength hydrochloric acid are added dropwise, at 20°-25° C. in the course of 30 minutes, with stirring, to a dark solution, obtained according to Example 1 of European Pat. No. 0,011,048 by reaction of 213 parts of 2,4-dinitrochlorobenzene with 42 parts of sodium hydroxide in 632 parts of methanol, subsequent hydrogenation on Pd/charcoal at 60° C. and then acetylation with 98 parts of acetic anhydride in the presence of 22 parts of magnesium oxide at 0°-5° C., of 6-methoxy-3-acetylamino-aniline which, according to "high performance liquid chromatography analysis" ("HPLC analysis") contains 8.9 parts of 2,4-bis-acetylaminoanisole and 3.5 parts of 2,4-diaminoanisole, as well as black decomposition products formed by oxidation, in addition to 153 parts of the target product. The mixture is subsequently stirred for 1 hour and cooled to 0°-5° C. and the 6-methoxy-3-acetylamino-aniline hydrochloride precipitated is isolated by filtration. The product is washed twice with 100 parts of methanol to give, after drying in vacuo, 188.5 parts of 6-methoxy-3-acetylamino-aniline hydrochloride, which, besides about 5% of magnesium chloride, contains no organic by-products detectable by thin-layer chromatography ("TLC") or HPLC analysis. The product isolated thus corresponds to 179.1 parts of 100% pure 6-methoxy-3-acetylamino-aniline hydrochloride, which corresponds to a yield of 82.7% of theory, based on the 2,4-dinitrochlorobenzene employed.

후처리

  1. customobtained
  2. customat 0°-5° C.
  3. customas well as black decomposition products formed by oxidation, in addition to 153 parts of the target product
  4. stirringThe mixture is subsequently stirred for 1 hour
  5. temperaturecooled to 0°-5° C.
  6. customthe 6-methoxy-3-acetylamino-aniline hydrochloride precipitated
  7. customis isolated by filtration
  8. washThe product is washed twice with 100 parts of methanol
  9. customto give
  10. dry with materialafter drying in vacuo, 188.5 parts of 6-methoxy-3-acetylamino-aniline hydrochloride, which, besides about 5% of magnesium chloride

출처 및 근거

ORD 기록
ord-30c2f68fe11b431ebc8eb3b1a6e331f1
출처 데이터셋
uspto-grants-1985_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04540815

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트