Trimethyl orthoformate → (4E)-6-t-butyl-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

HRID 2236443Notes

Reaction equation

HRID 2236443 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].[CH:17](OC)(OC)[O:18][CH3:19]>C(O)(=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

4

Reactant 2

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

Product 1

HCID 42625173(4E)-6-t-butyl-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dioneYield 79%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

An amount 200 mg (0.92 mmol) of 6-tert-butylisoquinoline-1,3(2H,4H)-dione is dissolved in acetic acid 1.0 mL followed by addition of trimethyl orthoformate (25 uL, 2.3 mmol). After, the mixture is heated at 90° C. for 1 h, and cooled to room temperature. The yellow solution evaporated to dryness. Small amounts of anhydrous ether is added and hexane. The yellow solid is collected with hexane to give 188 mg (79% yield) MS (ESI) m/z 260.2 (M+1). 1H NMR (300 MHz, DMSO-d6) 1.346 (S, 9H), 4.178 (S, 3H), 7.472-7.505 (dd, J=1.8 Hz, J=1.8 Hz 1H), 8.007 (d, J=8.52 Hz 2H), 8.31 (d, J=1.71 Hz 1H).

Workup

  1. temperaturecooled to room temperature
  2. customThe yellow solution evaporated to dryness
  3. additionSmall amounts of anhydrous ether is added
  4. customThe yellow solid is collected with hexane
  5. customto give 188 mg (79% yield)

Sources & evidence

ORD record
ord-b4d6474906be460580a56a15f1d19986
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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