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5-Amino-3-ethoxymethylisoquinoline → (S)-3-[(3-Ethoxymethylisoquinol-5-yl)imino]-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline

HRID 1577079
Notes
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Reaction equation

HRID 1577079 reaction equation
[I-].CS[C:4]1[S:5][CH2:6][C@@H:7]2[CH2:16][C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[CH2:9][N+:8]=12.[NH2:17][C:18]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:19]=1[CH:20]=[C:21]([CH2:28][O:29][CH2:30][CH3:31])[N:22]=[CH:23]2>N1C=CC=CC=1>[CH2:30]([O:29][CH2:28][C:21]1[N:22]=[CH:23][C:24]2[C:19]([CH:20]=1)=[C:18]([N:17]=[C:4]1[N:8]3[CH2:9][C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=4[CH2:16][C@H:7]3[CH2:6][S:5]1)[CH:27]=[CH:26][CH:25]=2)[CH3:31]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 128748535-Amino-3-ethoxymethylisoquinolineHCID 12874874(S)-3-Methylthio-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide

Product 1

HCID 12874877(S)-3-[(3-Ethoxymethylisoquinol-5-yl)imino]-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolineYield 67.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

(S)-3-Methylthio-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide (7.2 g) is added to a solution of 5-amino-3-ethoxymethylisoquinoline (4.1 g) in pyridine (150 cc). The suspension is stirred for 24 hours at a temperature of about 20° C. The insoluble material gradually dissolves. The solution is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 60° C. The residue is dissolved in a mixture of methylene chloride (100 cc) and N sodium hydroxide solution (100 cc). The organic phase is decanted, washed with water (50 cc), dried over magnesium sulphate and filtered and the filtrate is evaporated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa). The residue is recrystallised from isopropyl alcohol (80 cc). (S)-3-[(3-Ethoxymethylisoquinol-5-yl)imino]-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline (5.2 g) is thus obtained in the form of a pale yellow solid melting at 88° C.

Workup

  1. dissolutionThe insoluble material gradually dissolves
  2. concentrationThe solution is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 60° C
  3. dissolutionThe residue is dissolved in a mixture of methylene chloride (100 cc) and N sodium hydroxide solution (100 cc)
  4. customThe organic phase is decanted
  5. washwashed with water (50 cc)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customthe filtrate is evaporated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa)
  9. customThe residue is recrystallised from isopropyl alcohol (80 cc)

Sources & evidence

ORD record
ord-a6643c9ba35f4972bf8b5415f1331b31
Source dataset
uspto-grants-1981_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04287197

Reaction notes

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