Benzene → 2-Nitrophenylphenyl ether

HRID 27629

반응식

HRID 27629 반응식
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[C:11]1(O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:18](=[O:21])([O-])[O-].[K+].[K+].[CH:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>[Cu].CC(N(C)C)=O>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:21][C:18]1[CH:6]=[CH:7][CH:2]=[CH:3][C:4]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N+:8]([O-:10])=[O:9])([O-:10])=[O:9]

참가 물질

7

반응물 4

HCID 241BenzeneHCID 996PhenolHCID 69451-Chloro-2-nitrobenzeneHCID 11430Potassium Carbonate

생성물 1

HCID 215710152-Nitrophenylphenyl ether

시약·촉매·용매 2

HCID 23978Copper촉매HCID 31374Dimethylacetamide용매

실험 절차

In accordance with this sequence, a 1-chloro-2-nitrobenzene (5) is reacted with a phenol (6) a base such as potassium carbonate and activated copper where necessary in a solvent such as benzene of dimethyl acetamide with heat giving a 2-nitrophenylphenyl ether (7). This ether (7) is then reduced by conventional means (i.e. sodium hydrosulfite) to the phenoxyaniline (8). Isonicotinic acid is reacted with a mineral acid halide such as thionyl chloride heat or by heating at reflux in methylene chloride. The volatiles are evaporated and the residue is reacted with the phenoxyaniline (8) and a base such as triethylamine or potassium carbonate in a solvent such as tetrahydrofuran or benzene at a temperature from 25° to 80° for several hours giving a phenoxy-isonicotinanilide (9). This compound (9) is then reacted with phosphorous pentoxide and phosphorous oxychloride at reflux for several hours. The residue is reacted with ammonium hydroxide in ice and extracted in methylene chloride giving an 11-(4-pyridyl)-di-benz[b,f][1,4]oxazepine (10). This oxazepine (10) is then reacted with an alkyl halide in a solvent such as acetone or methylene chloride to produce (1), where R is as hereinbefore described which is the immediate precursor to the aforementioned anti-psychotic agents. To produce the 10,11-dihydro-11-(4-pyridyl)-dibenz[b,f][1,4]oxazepine (11), the compound (10), is treated with a reducing agent such as an alkali aluminum hydride in a solvent such as ether or benzene at reflux, quenched with water and extracted with methylene chloride. To produce the 10-alkyl-10,11-dihydro-11-(4-pyridyl)-dibenz[b,f][1,4]oxazepine (11), the compound (10) is dissolved in an alkanoic acid and treated with sodium borohydride. The compound (11) may be converted to the precursor (2) by reactions with an alkyl halide where R is as described above for compound (10).

후처리

  1. temperaturewith heat

출처 및 근거

ORD 기록
ord-cd6ddb2096b64b5999c9bccf8fdc4634
출처 데이터셋
uspto-grants-1980_09
특허 번호
US04221715

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