5-Amino-1-naphthol → 4-Fluoro-N-(5-hydroxynaphthalen-1-yl)-3-nitrobenzamide

HRID 326169

반응식

HRID 326169 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[F:13])[C:7](Cl)=[O:8])([O-:3])=[O:2].[NH2:14][C:15]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:16]=1[CH:17]=[CH:18][CH:19]=[C:20]2[OH:25]>C(#N)C.CN(C)C1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[F:13])[C:7]([NH:14][C:15]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:16]=1[CH:17]=[CH:18][CH:19]=[C:20]2[OH:25])=[O:8])([O-:3])=[O:2]

참가 물질

5

반응물 2

HCID 657465-Amino-1-naphtholHCID 27833474-Fluoro-3-nitrobenzoyl chloride

생성물 1

HCID 204625984-Fluoro-N-(5-hydroxynaphthalen-1-yl)-3-nitrobenzamide

시약·촉매·용매 2

HCID 949N,N-Dimethylaniline용매HCID 6342Acetonitrile용매

반응 조건

온도
50 °C

실험 절차

22.4 g of 3-nitro-4-fluorobenzoyl chloride (0.12 mols) were added dropwise at 0° C. to a suspension of 19.1 g of 5-amino-1-naphthol (0.12 mols) in 120 ml of acetonitrile and 14.2 g of N,N-dimethylaniline. The mixture was further stirred until it reached room temperature, and then heated for 30 minutes at 50° C. The yellow deposit was suction filtered and washed with acetonitrile. The deposit was dissolved in tetrahydrofurane and stirred with charcoal, filtered and the product was precipitated from the filtrate with petrol 50/75. Yield: 25.8 g=66% of the theoretical yield; mp. 235°-238° C.

후처리

  1. customreached room temperature
  2. filtrationThe yellow deposit was suction filtered
  3. washwashed with acetonitrile
  4. dissolutionThe deposit was dissolved in tetrahydrofurane
  5. stirringstirred with charcoal
  6. filtrationfiltered
  7. customthe product was precipitated from the filtrate with petrol 50/75

출처 및 근거

ORD 기록
ord-6d33a443335a4931be334c29a34512c5
출처 데이터셋
uspto-grants-1984_04
특허 번호
US04444867

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