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

HRID 507004
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HRID 507004 반응식
[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
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참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 79532,4,6-Trimethylpyridine용매
HCID 14798
Sodium Hydroxide
용매

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온도
200 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f1e1dbf5f39a4032b802a64ee6ee4a86
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07786115B2

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