Water → (4Z)-5-bromo-4-[[(3-hydroxy-4-methoxyphenyl)methylamino]methylidene]isoquinoline-1,3-dione

HRID 2236608노트

반응식

HRID 2236608 반응식
Cl.[OH:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH2:6][NH2:7].CCN(CC)CC.[Br:20][C:21]1[CH:30]=[CH:29][CH:28]=[C:27]2[C:22]=1/[C:23](=[CH:33]\OC)/[C:24](=[O:32])[NH:25][C:26]2=[O:31].O>CN(C)C=O>[Br:20][C:21]1[CH:30]=[CH:29][CH:28]=[C:27]2[C:22]=1/[C:23](=[CH:33]/[NH:7][CH2:6][C:5]1[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:3]([OH:2])[CH:4]=1)/[C:24](=[O:32])[NH:25][C:26]2=[O:31]

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 162176463-Hydroxy-4-methoxybenzylamine hydrochlorideHCID 68696086(4E)-5-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

생성물 1

HCID 178491079(4Z)-5-bromo-4-[[(3-hydroxy-4-methoxyphenyl)methylamino]methylidene]isoquinoline-1,3-dione수율 86.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 88.5 mg (0.468 mmol) of 3-hydroxy-4-methoxy-benzylamine hydrogen chloride in 1.8 mL of N,N-dimethylformamide (DMF) at RT under N2 is treated with 94.5 mg (0.936 mmol) of Et3N. (4E)-5-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (132 mg, 0.468 mmol) is added and the mixture is stirred for 3.5 h. Water is added and the product is collected, washed with H2O and Et2O and dried to give 163 mg (86%) of pale yellow amorphous solid: mp 204-206° C.; 1H NMR (DMSO-d6) δ 11.11 (s, 1H), 10.56 (m, 1H), 9.08 (s, 1H), 8.93 (d, 1H, J=13.6 Hz), 8.05 (d, 1H, J=6.9 Hz), 7.87 (d, 1H, J=6.9 Hz), 7.09 (m, 1H), 6.91 (d, 1H, J=8.07 Hz), 6.78 (m, 2H), 4.49 (d, 2H, J=5.37 Hz), 3.75 (s, 3H); HRMS (ESI) m/z calcd for C18H15BrN2O4 403.02880. found 403.02840 (M+H)+1.

후처리

  1. customthe product is collected
  2. washwashed with H2O and Et2O
  3. customdried

출처 및 근거

ORD 기록
ord-3f59e7ee767a46a4a1b8bf5d10ab0267
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07713994B2

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