Hydrochloric Acid → 5-Iodo-1-methyl-3,4-dihydroisoquinoline

HRID 926237Notes

Reaction equation

HRID 926237 reaction equation
[I:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]1C(=O)C(=O)O[C:7]12[CH3:17].IC1C=CC=CC=1CCNC(=O)C.C(Cl)(C(Cl)=O)=O.Cl>C(Cl)Cl>[I:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]=[C:7]2[CH3:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 65578Oxalyl chlorideHCID 86711313N-(2-iodophenethyl)acetamideHCID 867113147-iodo-10b-methyl-5,6-dihydro-2H-oxazolo[2,3-a]isoquinoline-2,3(10bH)-dione

Product 1

HCID 867113155-Iodo-1-methyl-3,4-dihydroisoquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-iodo-10b-methyl-5,6-dihydro-2H-oxazolo[2,3-a]isoquinoline-2,3(10bH)-dione. A solution of N-(2-iodophenethyl)acetamide (16.0 g, 55.3 mmol) in DCM (600 mL) under N2, was treated dropwise with (COCl)2 (5.33 mL, 60.9 mmol). The reaction was stirred at RT for 45 min and then cooled to 0° C. FeCl3 (10.8 g, 66.4 mmol) was then added and the mixture was allowed to slowly warm to RT and stirred at RT for 18 h. An aq. solution of 2N HCl (50 mL) was added and the mixture was stirred for 2 h. The organic phase was separated, dried over Na2SO4, filtered and concentrated in vacuo to provide the title compound as a brown solid (20.8 g) that was used as it is in the next step. UPLC-MS: MS 344.3 (M+H+); UPLC rt 1.10 min.

Workup

  1. temperaturecooled to 0° C
  2. temperatureto slowly warm to RT
  3. stirringstirred at RT for 18 h
  4. stirringthe mixture was stirred for 2 h
  5. customThe organic phase was separated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cd0d470aff3743f79c2a5c85023b8569
Source dataset
uspto-grants-2016_03
Patent number
US09284331B2

Reaction notes

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