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Hydrochloric Acid → 3-[3-Ethoxy-6-ethoxycarbonyl-5-(4-methoxyanilino)-1,8-naphthyridin-2-yl]acrylic acid hemihydrochloride

HRID 128628
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HRID 128628 반응식
[ClH:1].[CH2:2]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[N:13][C:14]=1[CH3:15])[N:11]=[CH:10][C:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:8]2[NH:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)[CH3:3].[C:30]([OH:34])(=[O:33])[CH:31]=O.C(=O)(O)[O-].[Na+].Cl>O.C(O)(=O)C>[ClH:1].[CH2:2]([O:4][C:5]1[C:14]([CH:15]=[CH:31][C:30]([OH:34])=[O:33])=[N:13][C:12]2[C:7]([CH:6]=1)=[C:8]([NH:21][C:22]1[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=1)[C:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][N:11]=2)[CH3:3].[CH2:2]([O:4][C:5]1[C:14]([CH:15]=[CH:31][C:30]([OH:34])=[O:33])=[N:13][C:12]2[C:7]([CH:6]=1)=[C:8]([NH:21][C:22]1[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=1)[C:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][N:11]=2)[CH3:3]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 760Glyoxylic AcidHCID 516892Sodium BicarbonateHCID 19374282Ethyl 4-(4-methoxyanilino)-6-ethoxy-7-methyl-1,8-naphthyridine-3-carboxylate hydrochloride

생성물 1

HCID 1317191773-[3-Ethoxy-6-ethoxycarbonyl-5-(4-methoxyanilino)-1,8-naphthyridin-2-yl]acrylic acid hemihydrochloride

시약·촉매·용매 2

HCID 176Acetic Acid용매
HCID 962Water용매

실험 절차

A mixture of ethyl 6-ethoxy-4-(4-methoxyanilino)-7-methyl-1,8-naphthyridine-3-carboxylate hydrochloride (4.76 g), glyoxylic acid (1.73 g) and glacial acetic acid (50 ml) was boiled under reflux for 24 hours. The mixture was cooled and a solid was collected by filtration. The filtrate was acidified with concentrated hydrochloric acid and filtered to give a second crop of solid. The two crops of solid were combined, stirred in water and the mixture basified with sodium bicarbonate. The pH of the mixture was adjusted to pH 6 with concentrated hydrochloric acid and the mixture was extracted with ethyl acetate and then with dichloromethane. The combined organic extracts were washed with water, dried and evaporated. The residue was triturated with ethyl acetate and then filtered to give 3-[3-ethoxy-6-ethoxycarbonyl-5-(4-methoxyanilino)-1,8-naphthyridin-2-yl]acrylic acid hemihydrochloride, m.p. 259°-261° C.

후처리

  1. temperatureunder reflux for 24 hours
  2. temperatureThe mixture was cooled
  3. filtrationa solid was collected by filtration
  4. filtrationfiltered
  5. customto give a second crop of solid
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe combined organic extracts were washed with water
  8. customdried
  9. customevaporated
  10. customThe residue was triturated with ethyl acetate
  11. filtrationfiltered

출처 및 근거

ORD 기록
ord-07efd22cd5d24ce2b55488eaf85c7440
출처 데이터셋
uspto-grants-1995_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05464781

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