4,7-dichloro-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)-3-(hydroxymethyl)-1-pentyl-1,3-dihydro-2H-indol-2-one

HRID 425524Notes

Reaction equation

HRID 425524 reaction equation
BrC1C=CC=C2C=1C(C1C(O)=CC3OCOC=3C=1)[C:5](=[O:16])N2CCCCC.[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]>>[Cl:27][C:28]1[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]2[C:29]=1[C: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)([CH2:5][OH:16])[C:31](=[O:43])[N:32]2[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]

Participants

3

Reactant 2

HCID 588724464,7-dichloro-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-indol-2-oneHCID 588725004-bromo-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-indol-2-one

Product 1

HCID 588724744,7-dichloro-3-(6-hydroxy-1,3-benzodioxol-5-yl)-3-(hydroxymethyl)-1-pentyl-1,3-dihydro-2H-indol-2-one

Procedure

Following the procedure as described in PREPARATION 1E, and making non-critical variations to replace 4-bromo-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-indol-2-one with 4,7-dichloro-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-indol-2-one, the title compound was obtained (94%) as a gummy solid: MS (ES+) m/z 439.3 (M+1).

Sources & evidence

ORD record
ord-e64dfd6ff07e4178a6defbf5c37c8fa2
Source dataset
uspto-grants-2012_01
Patent number
US08106087B2

Reaction notes

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