Hydrochloric Acid → 6-chloro-1,3-dioxo-1H-benz[de]isoquinoline-2(3H)-acetic acid

HRID 126688노트

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HRID 126688 반응식
[CH:1]1[CH:10]=[C:9]2[C:11]([O:13][C:14](=[O:15])[C:7]3=[C:8]2[C:3](=[C:4]([Cl:16])[CH:5]=[CH:6]3)[CH:2]=1)=O.[OH-].[Na+].[NH2:19][CH2:20][C:21]([OH:23])=[O:22].Cl>>[Cl:16][C:4]1[CH:5]=[CH:6][C:7]2[C:14](=[O:15])[N:19]([CH2:20][C:21]([OH:23])=[O:22])[C:11](=[O:13])[C:9]3[C:8]=2[C:3]=1[CH:2]=[CH:1][CH:10]=3

참가 물질

5

반응물 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 14798Sodium HydroxideHCID 776721H,3H-Naphtho[1,8-cd]pyran-1,3-dione, 6-chloro-

생성물 1

HCID 150089276-chloro-1,3-dioxo-1H-benz[de]isoquinoline-2(3H)-acetic acid수율 74.3%

실험 절차

4-Chloro-1,8-naphthalic anhydride (20.0 g, 0.086 mole; commercial material purified by crystallization from toluene) was suspended in an aqueous 1 N sodium hydroxide solution (95 ml) of glycine (3.8 g, 0.095 mole). The mixture was stirred and refluxed for one hr, after which time a clear solution had resulted. The mixture was rendered acidic with conc hydrochloric acid. The resulting precipitate was collected and dried. Crystallization of the precipitate from anhydrous ethanol afforded 18.5 g of 6-chloro-1,3-dioxo-1H-benz[de]isoquinoline-2(3H)-acetic acid, mp 260° C.; UV (MeOH) 235,339 and 352 nm, ε=41,310, 15,190 and 13,700, respectively; IR (CHCl3) 1725, 1705 and 1670 cm-1 ; NMR (DMSO-d6) δ4.6 (s, 2H), 6.0 (m, 1H), 7.9 (m, 2H), 8.45 (m, 3H); Anal. Calc'd.: C, 58.05%; H, 2.78%; N, 4.83%; Found: C, 58.16%; H, 2.74%; N, 4.69%.

후처리

  1. temperaturerefluxed for one hr
  2. customafter which time a clear solution had resulted
  3. customThe resulting precipitate was collected
  4. customdried
  5. customCrystallization of the precipitate from anhydrous ethanol

출처 및 근거

ORD 기록
ord-0907f8767caa4c5480ee5c245eaed4f2
출처 데이터셋
uspto-grants-1981_03
특허 번호
US04254108

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