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

HRID 2236608ノート

反応式

HRID 2236608 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-3f59e7ee767a46a4a1b8bf5d10ab0267
出典データセット
uspto-grants-2010_05
特許番号
US07713994B2

反応ノート

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