Hydrogen Bromide → 3-Hydroxy-4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridinium bromide

HRID 1155342노트

반응식

HRID 1155342 반응식
[OH:1][C:2]1[C:10]2[CH2:9][CH2:8][N:7](C(OC)=O)[CH2:6][C:5]=2[O:4][N:3]=1.[BrH:15].[K+].[Br-].CO>C(O)(=O)C>[Br-:15].[OH:1][C:2]1[C:10]2[CH2:9][CH2:8][NH:7][CH2:6][C:5]=2[O:4][NH+:3]=1

참가 물질

6

반응물 4

HCID 260Hydrogen BromideHCID 887MethanolHCID 253877Potassium BromideHCID 178501908HCID 178501908, 화합물

생성물 1

HCID 700825683-Hydroxy-4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridinium bromide

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A solution of methyl 3-hydroxy-4,5,6,7-tetrahydroisoxazolo[5, 4-c]-pyridine-6-carboxylate (309 mg; 1.6 mmol) in a solution of hydrogen bromide in glacial acetic acid (3 ml; 43%) was refluxed for 15 minutes. Upon evaporation to dryness in vacuo the residue was treated with the same reagent (3 ml) for further 15 minutes. Evaporation of the reaction mixture to dryness in vacuo and recrystallization (methanol-ether) of the residue gave Ia (salt) (193 mg; 56%) as faintly reddish crystals, m.p. 162-163° C. (decomp.). IR (KBr): 3700-3300 (m), 3070 (s), 3000-2300 (several bands, m-s), 1670 (m), 1580 (m), 1525 (s), 1505 (w) cm-1. UV (methanol): <210 nm. 1H NMR [D2O (sodium 3-(trimethylsilyl) propanesulfonate was used as an internal standard)]: δ4.77 (ca. 5 H, s), 4.43 (2 H, t, J 1 Hz), 3.7- 3.4 (2 H, q, J 6 and 7 Hz), 3.0-2.7 (2 H, t).

후처리

  1. customUpon evaporation to dryness in vacuo the residue
  2. additionwas treated with the same reagent (3 ml) for further 15 minutes
  3. customEvaporation of the reaction mixture to dryness
  4. customin vacuo and recrystallization (methanol-ether) of the residue
  5. customgave Ia (salt) (193 mg; 56%) as faintly reddish crystals, m.p. 162-163° C. (decomp.)

출처 및 근거

ORD 기록
ord-eaa2bb7851074f4cb58f61a46e6f16fd
출처 데이터셋
uspto-grants-1981_11
특허 번호
US04301287

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