4,7-dichloro-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-indol-2-one → 4,7-dichloro-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-indol-2-one

HRID 645066Notes

Reaction equation

HRID 645066 reaction equation
C1(CCN2C3C(=CC=CC=3)C(O)(C3C(O)=CC4OCOC=4C=3)C2=O)CC1.[Cl:27][C:28]1[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]2[C:29]=1[C:30](O)([C:44]1[C:52]([OH:53])=[CH:51][C:47]3[O:48][CH2:49][O:50][C:46]=3[CH:45]=1)[C:31](=[O:43])[N:32]2[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]>>[Cl:27][C:28]1[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]2[C:29]=1[CH:30]([C:44]1[C:52]([OH:53])=[CH:51][C:47]3[O:48][CH2:49][O:50][C:46]=3[CH:45]=1)[C:31](=[O:43])[N:32]2[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]

Participants

3

Reactant 2

HCID 120044014,7-dichloro-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-indol-2-oneHCID 588725381-(2-cyclopropylethyl)-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 588724464,7-dichloro-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-indol-2-one

Procedure

Following the procedure as described in PREPARATION 2C, and making non-critical variations to replace 1-(2-cyclopropylethyl)-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1,3-dihydro-2H-indol-2-one with 4,7-dichloro-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-indol-2-one, the title compound was obtained (72%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 7.27-7.23 (m, 1H), 7.03 (d, 1H), 6.55 (s, 1H), 6.04 (s, 1H), 5.84 (dd, 2H), 5.03 (s, 1H), 4.09-3.99 (m, 2H), 1.72-1.62 (m, 2H), 1.33-1.24 (m, 4H), 0.86 (t, 3H); MS (ES+) m/z 409.2 (M+1).

Sources & evidence

ORD record
ord-b7fda0bd97464932969c3aa0f919c52e
Source dataset
uspto-grants-2010_04
Patent number
US07700641B2

Reaction notes

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