Trimethyl orthoformate → 6-tert-Butyl-4-methoxymethylene-4H-isoquinoline-1,3-dione

HRID 2236491Notes

Reaction equation

HRID 2236491 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[NH:10][C:9](=[O:16])[CH2:8]2)([CH3:4])([CH3:3])[CH3:2].[CH3:17][O:18][CH:19](OC)OC>CN(C)C=O.C(OC(=O)C)(=O)C>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[NH:10][C:9](=[O:16])[C:8]2=[CH:17][O:18][CH3:19])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 9005Trimethyl orthoformateHCID 426251726-tert-butyl-4H-isoquinoline-1,3-dione

Product 1

HCID 686925676-tert-Butyl-4-methoxymethylene-4H-isoquinoline-1,3-dione

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
120 °C

Procedure

6-tert-Butyl-4H-isoquinoline-1,3-dione (45 mg, 0.21 mmol) is dissolved in N,N-dimethylformamide (1 mL) and acetic anhydride (2 mL). Trimethylorthoformate (0.2 mL) is added and the mixture is heated to 120° C. for 1 hour. The volatiles were removed under vacuum and the residue passed through a column to afford the crude product, is used directly in the next step. MS (ESI): 258.3 (M−1)−1.

Workup

  1. customThe volatiles were removed under vacuum

Sources & evidence

ORD record
ord-2db21f0d9f9e4e1da4c3f22cfbf48305
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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