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

HRID 1155342ノート

反応式

HRID 1155342 の反応式
[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

参加物

6

反応物 4

HCID 260Hydrogen BromideHCID 887MethanolHCID 253877Potassium BromideHCID 178501908HCID 178501908、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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).

後処理

  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.)

出典と根拠

ORDレコード
ord-eaa2bb7851074f4cb58f61a46e6f16fd
出典データセット
uspto-grants-1981_11
特許番号
US04301287

反応ノート

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