Isoquinoline → HCID 67308641, compound

HRID 2061592Notes

Reaction equation

HRID 2061592 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[CH3:11][O:12]/[C:13](=[CH:19]/[C:20](=[CH2:26])[O:21][Si](C)(C)C)/[O:14][Si](C)(C)C.Cl[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29].[NH4+].[Cl-]>C(Cl)Cl>[CH3:11][O:12][C:13](=[O:14])[CH2:19][C:20](=[O:21])[CH2:26][CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]1[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29]

Participants

6

Reactant 4

HCID 8405IsoquinolineHCID 10387Benzyl chloroformateHCID 25517Ammonium ChlorideHCID 11010738(4Z)-4-Methoxy-2,2,8,8-tetramethyl-6-methylene-3,7-dioxa-2,8-disilanon-4-ene

Product 1

HCID 67308641HCID 67308641, compoundYield 111.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the mixture of isoquinoline (24) (2.05 g, 15.9 mmol) in 150 mL of CH2Cl2 at 0° C. was added (Z)-4-methoxy-2,2,8,8-tetramethyl-6-methylene-3,7-dioxa-2,8-disilanon-4-ene (25) (8.29 g, 31.8 mmol), followed by benzyl chloroformate (2.7 mL, 19.1 mmol). After stirring at room temperature overnight, 100 mL of NH4Cl (aq) was added to the mixture. The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (3×100 mL). The combined organic extracts were dried over Na2SO4. After the desiccant was filtered off, the organic extracts were concentrated under reduced pressure to provide (26) as a yellow oil (6.73 g). 1H NMR indicated about a 1:2 ratio of keto:enol tautomers. This crude oil was used in the next reaction without further purification.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with CH2Cl2 (3×100 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationAfter the desiccant was filtered off
  5. concentrationthe organic extracts were concentrated under reduced pressure

Sources & evidence

ORD record
ord-9ebe0393bffb42e98c5296370cb9c7e0
Source dataset
uspto-grants-2012_10
Patent number
US08283358B2

Reaction notes

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