Water → HCID 59341073, compound

HRID 14626Notes

Reaction equation

HRID 14626 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[C:15]2[C:10](=[C:11]([O:18][CH3:19])[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=2)[C:9]([CH2:20][N:21]2[C:29](=[O:30])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]2=[O:31])=[N:8][CH2:7]1)=[O:5])[CH3:2].O>C1C=CC=CC=1.O=[Mn]=O>[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[C:11]([O:18][CH3:19])[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=2)[C:9]([CH2:20][N:21]2[C:22](=[O:31])[C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:29]2=[O:30])=[N:8][CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 962WaterHCID 68614648HCID 68614648, compound

Product 1

HCID 59341073HCID 59341073, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 241BenzeneSolvent

Procedure

Silica gel (5 g) and MnO2 (4.60 g, 52.9 mmol) were ground to a homogenous consistency and the mixture was added to a solution of 1-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-6,8-dimethoxy-3,4-dihydro-isoquinoline-4-carboxylic acid ethyl ester (Note 1) (1.39 g, 3.53 mmol) in 180 mL of benzene. The reaction flask, equipped with a Dean-Stark trap and a condenser, was then heated to 100° C., with azeotropic removal of water (18 ml). After 4 hours, the reaction was cooled to room temperature and filtered through a plug of celite, rinsing with 3% MeOH in DCM. The filtrate was concentrated to give 1.30 g (94%) of 1-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-6,8-dimethoxy-isoquinoline-4-carboxylic acid ethyl ester as a white solid. H1-NMR (CDCl3): δ, 8.85 (s, 1H), 8.07 (d, 111, J=2.1 Hz), 7.92 (m, 2H), 7.75 (m, 2H), 6.62 (d, 1H, J=2.4 Hz), 5.62 (s, 2H), 4.36 (q, 2H, J=7.4), 4.03 and 3.98 (s, 3H each), 1.36 (t, 3H, J=6.9 Hz).

Workup

  1. customThe reaction flask, equipped with a Dean-Stark trap and a condenser
  2. filtrationfiltered through a plug of celite
  3. washrinsing with 3% MeOH in DCM
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-722cf82db39c409eb44cd3dedcb941d6
Source dataset
uspto-grants-2010_06
Patent number
US07732446B1

Reaction notes

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