Water → Ethyl 4-azido-7-chloroquinoline-3-carboxylate

HRID 1862820노트

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HRID 1862820 반응식
[N-:1]=[N+:2]=[N-:3].[Na+].[CH2:5]([O:7][C:8]([C:10]1[CH:11]=[N:12][C:13]2[C:18]([C:19]=1Cl)=[CH:17][CH:16]=[C:15]([Cl:21])[CH:14]=2)=[O:9])[CH3:6].O>CN(C)C=O>[CH2:5]([O:7][C:8]([C:10]1[CH:11]=[N:12][C:13]2[C:18]([C:19]=1[N:1]=[N+:2]=[N-:3])=[CH:17][CH:16]=[C:15]([Cl:21])[CH:14]=2)=[O:9])[CH3:6]

참가 물질

5

반응물 3

HCID 962WaterHCID 33557Sodium AzideHCID 12256460Ethyl 4,7-dichloroquinoline-3-carboxylate

생성물 1

HCID 3690236Ethyl 4-azido-7-chloroquinoline-3-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Sodium azide (0.62 g; 0.009 M) was suspended in a solution of ethyl-4,7-dichloroquinoline-3-carboxylate E. F. Elslager, et al., J. Med. Pharm, Chem, 5, 550 (1962) (1.75 g; 0.006 M) in dry dimethyl formamide (20 ml) and this mixture stirred at ambient temperatures. After 18 hr. the mixture was poured into reapidly stirred water (200 ml), the resultant precipitate filtered off, dried at the pump and then recrystallised from ethanol (8 ml/g), 1.27 g (71%), m.p. 94.5° C., (Found: C, 51.7; H, 3.4; N, 20.2; Cl, 12.9% C12H9N4O2Cl requires C, 52.0; H, 3.3; N, 20.2; Cl, 12.8%); max (KBr) 2140, 1722, 1390, 1372, 1274, 1239, 1199 and 1058 cm-1, (CDCl3) 1.48 (t) and 4.55 (m) (CH3CH2), 7.59 (m), 8.11 (d), 8.32 (d) and 9.29 (s) (aromatic H's) m/e 276 (M+, 14%), 248 (9%), 218 (22%), 154 (29% 152 (100%).

후처리

  1. filtrationthe resultant precipitate filtered off
  2. customdried at the pump
  3. customrecrystallised from ethanol (8 ml/g), 1.27 g (71%), m.p. 94.5° C., (Found: C, 51.7; H, 3.4; N, 20.2; Cl, 12.9% C12H9N4O2Cl requires C, 52.0; H, 3.3; N, 20.2; Cl, 12.8%)

출처 및 근거

ORD 기록
ord-2f02153f3559465c89cf9b203bd50cc8
출처 데이터셋
uspto-grants-1979_09
특허 번호
US04166817

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