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Hydrochloric Acid → N-Cyclopropyl-3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide

HRID 506963
ノート
印刷プレビュー

反応式

HRID 506963 の反応式
[CH:1]1([NH:4][C:5](=[O:26])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][C:17]([O:23]C)=[CH:18][CH:19]=4)[C:14]3=[O:25])[CH:7]=2)[CH2:3][CH2:2]1.[I-].[Li+].[OH-].[Na+].Cl>N1C(C)=CC(C)=CC=1C>[CH:1]1([NH:4][C:5](=[O:26])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][C:17]([OH:23])=[CH:18][CH:19]=4)[C:14]3=[O:25])[CH:7]=2)[CH2:3][CH2:2]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66321Lithium iodideHCID 11530361N-cyclopropyl-3-(7-methoxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide

生成物 1

HCID 11515516N-Cyclopropyl-3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide収率 69.3%

試薬・触媒・溶媒 1

HCID 7953
2,4,6-Trimethylpyridine
溶媒

反応条件

温度
200 °C

実験手順

A stirred suspension of N-cyclopropyl-3-(7-methoxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide (845 mg) and lithium iodide (585 mg) in 2,4,6 collidine (10 ml) was heated under microwave irradiation conditions (Personal Chemistry Emrys Optimizer with 300 W magnetron) at 200° C. for 90 minutes. The mixture was dissolved using 2N NaOH and re-acidified using 2N HCl. The aqueous phase was extracted with ethyl acetate (×4) and the combined organic layers concentrated. The residue was triturated with 2N HCl and the solid collected by filtration, washed with diethyl ether and air dried to yield N-cyclopropyl-3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide as a brown solid (562 mg); NMR Spectrum: (DMSOd6) 0.55 (m, 2H), 0.69 (m, 2H), 2.10 (s, 3H), 2.85 (m, 1H), 6.66 (d, 1H), 7.11 (d, 1H), 7.24 (d, 1H), 7.49 (d, 1H), 7.60 (s, 1H), 7.61 (d, 1H), 7.73 (s, 1H), 7.88 (d, 1H), 8.43 (d, 1H), 10.00 (s, 1H); Mass Spectrum: M+Na+ 357.

後処理

  1. dissolutionThe mixture was dissolved
  2. extractionThe aqueous phase was extracted with ethyl acetate (×4)
  3. concentrationthe combined organic layers concentrated
  4. customThe residue was triturated with 2N HCl
  5. filtrationthe solid collected by filtration
  6. washwashed with diethyl ether and air
  7. customdried

出典と根拠

ORDレコード
ord-3152026f5c564506847015f18324cd8e
出典データセット
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07786115B2

反応ノート

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