Hydrochloric Acid → HCID 178490398, compound

HRID 616688Notes

Reaction equation

HRID 616688 reaction equation
[NH2:1][N:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12].C(O[C:16](=[NH:25])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=1)C.Cl>>[CH3:24][O:23][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[C:16]([NH:1][N:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12])=[NH:25]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 1909912-amino-3,4-dihydroisoquinolin-1(2H)-oneHCID 12282162Ethyl 3-methoxybenzimidate3×

Product 1

HCID 178490398HCID 178490398, compound

Conditions

Temperature
125 °C

Procedure

A mixture of 16.2 g. of 2-amino-3,4-dihydro-1(2H)-isoquinolinone (0.10 mole), 27 g. of m-methoxybenzimidic acid ethyl ester (0.15 mole) and 2.15 g. of the hydrochloride of m-methoxybenzimidic acid ethyl ester is heated under vacuum (200 mm Hg.) for 5 hours at about 90° C and for 2 hours at about 125° C. Then 3.50 g. of m-methoxybenzimidic acid ethyl ester (0.02 mole) is added and the mixture is heated for a further 16 hours at about 125° C under vacuum. All volatile materials are eliminated by distilling off at 125° C and 5 mm Hg. The solid residue may be used as such for the cyclization step or, after washing with aqueous sodium bicarbonate and water, may be purified by crystallization from ethanol to isolate the intermediate III, 2-(m-methoxybenzimidoylamino)-3,4-dihydro-1-(2H)-isoquinolinone (m.p. 176°-177° C). The crude reaction product is cyclized by heating for five hours in 150 ml. of ethanol containing 1.2 g. of 80% sodium hydride (0.040 mole). The reaction mixture is then evaporated to dryness in vacuo and then dissolved in dichloromethane. The organic solution after washing with water is evaporated and the crude residual compound is crystallized from 50% ethanol, yielding 20 g. (72%) of the title compound, m.p. 94°-96° C.

Workup

  1. additionA mixture of 16.2 g
  2. distillationby distilling off at 125° C
  3. washafter washing with aqueous sodium bicarbonate and water
  4. custommay be purified by crystallization from ethanol

Sources & evidence

ORD record
ord-90689c4d48d04ea89b4c82275e256cb9
Source dataset
uspto-grants-1978_02
Patent number
US04075341

Reaction notes

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