1-hexyl-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1,3-dihydro-2H-indol-2-one → 1-hexyl-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1,3-dihydro-2H-indol-2-one

HRID 1259623Notes

Reaction equation

HRID 1259623 reaction equation
C1(CCN2C3C(=CC=CC=3)C(O)(C3C(O)=CC4OCOC=4C=3)C2=O)CC1.[CH2:27]([N:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:35](O)([C:42]2[C:50]([OH:51])=[CH:49][C:45]3[O:46][CH2:47][O:48][C:44]=3[CH:43]=2)[C:34]1=[O:53])[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>>[CH2:27]([N:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]([C:42]2[C:50]([OH:51])=[CH:49][C:45]3[O:46][CH2:47][O:48][C:44]=3[CH:43]=2)[C:34]1=[O:53])[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

3

Reactant 2

HCID 120044031-hexyl-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-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 588725471-hexyl-3-(6-hydroxy-1,3-benzodioxol-5-yl)-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 1-hexyl-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1,3-dihydro-2H-indol-2-one, the title compound was obtained (98%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 7.38-7.13 (m, 3H), 6.94 (d, 1H), 6.60 (s, 1H), 6.32 (s, 1H), 5.84 (dd, 2H), 5.02 (s, 1H), 3.74-3.63 (m, 2H), 1.70-1.61 (m, 2H), 1.37-1.19 (m, 6H), 0.83 (t, 3H); MS (ES+) m/z 354.2 (M+1).

Sources & evidence

ORD record
ord-eaa34485045a4d87907917eb3ee97a80
Source dataset
uspto-grants-2013_06
Patent number
US08466188B2

Reaction notes

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