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

HRID 507004
ノート
印刷プレビュー

反応式

HRID 507004 の反応式
[CH:1]1([NH:4][C:5](=[O:27])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[CH:22]=[C:21]([CH3:23])[C:20]4[C:15](=[CH:16][C:17]([O:24]C)=[CH:18][CH:19]=4)[C:14]3=[O:26])[CH:7]=2)[CH2:3][CH2:2]1.[I-].[Li+].Cl>N1C(C)=CC(C)=CC=1C.[OH-].[Na+]>[CH:1]1([NH:4][C:5](=[O:27])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[CH:22]=[C:21]([CH3:23])[C:20]4[C:15](=[CH:16][C:17]([OH:24])=[CH:18][CH:19]=4)[C:14]3=[O:26])[CH:7]=2)[CH2:2][CH2:3]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 3

HCID 313Hydrochloric AcidHCID 66321Lithium iodideHCID 11710269N-cyclopropyl-3-(7-methoxy-4-methyl-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide

生成物 1

HCID 67018616N-cyclopropyl-3-(7-hydroxy-4-methyl-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide

試薬・触媒・溶媒 2

HCID 79532,4,6-Trimethylpyridine溶媒
HCID 14798
Sodium Hydroxide
溶媒

反応条件

温度
200 °C

実験手順

N-cyclopropyl-3-(7-methoxy-4-methyl-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide (262 mg, 0.72 mmol) and lithium iodide (174 mg) were stirred in 2,4,6-collidine (3 ml) and heated under microwave irradiation conditions (Personal Chemistry Emrys Optimizer with 300 W magnetron) at 200° C. for 1.5 hour and then allowed to cool. The reaction mixture was dissolved in 2N NaOH and then re-acidified with 2N HCl solution. The aqueous phase was extracted with ethyl acetate (×4) and the combined organic layers were concentrated. The residue was triturated with 1N HCl, the solid was collected by filtration, washed with water, diethyl ether, and air dried to give N-cyclopropyl-3-(7-hydroxy-4-methyl-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide as an off white solid (207 mg); NMR Spectrum: (DMSOd6) 0.56 (m, 2H), 0.69 (m, 2H), 2.09 (s, 3H), 2.24 (s, 3H), 2.86 (m, 1H), 7.00 (s, 1H), 7.31 (d, 1H), 7.48 (d, 1H), 7.62-7.65 (m, 2H), 7.74 (s, 1H), 7.85 (d, 1H), 8.45 (d, 1H), 10.04 (s, 1H); Mass Spectrum: M+H+ 349.

後処理

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

出典と根拠

ORDレコード
ord-f1e1dbf5f39a4032b802a64ee6ee4a86
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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