Acetic Anhydride → 1-(4,4-dimethyl-7-nitro-3,4-dihydro-1H-isoquinolin-2-yl)ethanone

HRID 969671Notes

Reaction equation

HRID 969671 reaction equation
[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[CH:9][CH:10]=2)[CH2:5][NH:4][CH2:3]1.CCN(C(C)C)C(C)C.[CH3:25][C:26](OC(C)=O)=[O:27]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[CH:9][CH:10]=2)[CH2:5][N:4]([C:26](=[O:27])[CH3:25])[CH2:3]1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 219596554,4-Dimethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 219595651-(4,4-dimethyl-7-nitro-3,4-dihydro-1H-isoquinolin-2-yl)ethanone

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(dimethylamino)pyridine (0.125 g, 1.02 mmol), 4,4-dimethyl-7-nitro-1,2,3,4-tetrahydro-isoquinoline (0.21 g, 1.02 mmol), DIEA (0.53 mL, 3.06 mmol), and Ac2O (0.19 mL, 2.04 mmol) in 7 mL of CH2Cl2 was stirred at RT under N2 for two days. The volatiles were removed under vacuum. The residue was partitioned between EtOAc and brine, and the organic portion was dried with Na2SO4, filtered, and concentrated. The crude material was purified by flash column chromatography (2-3% MeOH in CH2Cl2), to yield the desired compound as a light yellowish solid. MS (ES+): 249.3 (M+H)+. Calc'd for C13H16N2O3-248.28.

Workup

  1. customThe volatiles were removed under vacuum
  2. customThe residue was partitioned between EtOAc and brine
  3. dry with materialthe organic portion was dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by flash column chromatography (2-3% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-d1f9a01c9f3e470587ef7c783abd9c66
Source dataset
uspto-grants-2007_12
Patent number
US07307088B2

Reaction notes

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