HCID 22057577, compound → Ethyl 1-(aminomethyl)-6,8-dimethoxyisoquinoline-4-carboxylate

HRID 14627Notes

Reaction equation

HRID 14627 reaction equation
[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]2C(=O)C3C(=CC=CC=3)C2=O)=[N:8][CH:7]=1)=[O:5])[CH3:2].O.NN.C(O)C>>[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][NH2:21])=[N:8][CH:7]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 22057577HCID 22057577, compoundHCID 59341073HCID 59341073, compound

Product 1

HCID 11778955Ethyl 1-(aminomethyl)-6,8-dimethoxyisoquinoline-4-carboxylateYield 123.5%

Conditions

Temperature
40 °C

Procedure

To a solution of 1-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-6,8-dimethoxy-isoquinoline-4-carboxylic acid ethyl ester (1.22 g, 2.90 mmol) in 80 mL of absolute ethanol hydrazine monohydrate (1.59 g, 31.8 mmol) was added and the mixture was stirred under a nitrogen atmosphere at 40° C. After 4 h, the reaction was cooled to room temperature, and the phthalhydrazide precipitate was removed by filtration, rinsing with ethanol. The filtrate was concentrated under reduced pressure to give 1.04 g of crude 1-aminomethyl-6,8-dimethoxy-isoquinoline-4-carboxylic acid ethyl ester, which was used directly the next step. H1-NMR (DMSO): δ, 8.84 (s, 1H), 7.81 (d, 1, J=2.4 Hz), 6.76 (d, 1H, J=2.3 Hz), 4.36 (q, 2H, J=7.13), 4.32 (s, 2H), 3.95 and 3.88 (s, 3H each), 1.35 (t, 3H, J=7.2 Hz); MS: APCI (M+H) calc'd for C15H18N2O4+H 291.3; found 291.1.

Workup

  1. temperaturethe reaction was cooled to room temperature
  2. customthe phthalhydrazide precipitate was removed by filtration
  3. washrinsing with ethanol
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8c945fe9c735460ba4ece0143d86b834
Source dataset
uspto-grants-2010_06
Patent number
US07732446B1

Reaction notes

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