Hydrochloric Acid → HCID 59558356, compound

HRID 1175122Notes

Reaction equation

HRID 1175122 reaction equation
[Na].[C:2]([O:9][CH2:10][CH3:11])(=[O:8])[C:3]([O:5]CC)=O.[Cl:12][C:13]1[N:14]=[CH:15][C:16]2[CH2:17][CH2:18][CH2:19][C:20](=[O:23])[C:21]=2[CH:22]=1.Cl>CCO>[CH2:10]([O:9][C:2](=[O:8])[C:3]([CH:19]1[CH2:18][CH2:17][C:16]2[CH:15]=[N:14][C:13]([Cl:12])=[CH:22][C:21]=2[C:20]1=[O:23])=[O:5])[CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 5360545SodiumHCID 595583933-chloro-7,8-dihydroisoquinolin-5(6H)-one

Product 1

HCID 59558356HCID 59558356, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium (253 mg; 11 mmol) is added portion-wise to EtOH (6 ml). After complete dissolution, diethyl oxalate (800 mg; 5.5 mmol) is introduced at room temperature, followed by 3-chloro-7,8-dihydro-6H-isoquinolin-5-one (1 g; 5.5 mmol) in EtOH (30 ml). The reaction mixture is stirred for 3 h at room temperature, poured on 1 N HCl and extracted with TBME three times. The organic phases are combined, dried over Na2SO4 and evaporated to dryness, yielding the desired product as orange oil. 1H-NMR (400 MHz; DMSO-d6): 8.47 (s, 1H); 7.68 (s, 1H); 4.29 (q, 2H); 3.42 (bs, 1H); 2.86 (bt, 2H); 2.63 (bt, 2H); 1.29 (t, 3H).

Workup

  1. additionis introduced at room temperature
  2. extractionextracted with TBME three times
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-05dfb0247c4344748bcc5a0e698cb3e6
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

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