Sodium Bicarbonate → HCID 86623346, compound

HRID 1986359Notes

Reaction equation

HRID 1986359 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([NH2:18])=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(O)=O.[Na+].[Cl:24][C:25]1[CH:30]=[C:29](Cl)[C:28]([N+:32]([O-:34])=[O:33])=[CH:27][N:26]=1>C(O)C.C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([NH:18][C:29]3[C:28]([N+:32]([O-:34])=[O:33])=[CH:27][N:26]=[C:25]([Cl:24])[CH:30]=3)=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 122757652,4-Dichloro-5-nitropyridineHCID 22061016tert-Butyl 7-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 86623346HCID 86623346, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the 7-amino-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (5.2 g, 21.0 mmol) in ethanol (60 mL) and THF (15 mL) was added NaHCO3 (5.3 g, 63.0 mmol) followed by the product of Example 1, Step 3 (4.05 g, 21.0 mmol), and the reaction mixture was stirred overnight rt. The reaction mixture was concentrated then taken up in EtOAc and H2O extracted with EtOAc, the organic layers were combined, dried over MgSO4, filtered, and concentrated. The crude material was crystallized from EtOAc/hexane to give the title compound as a yellow solid. MS (ES+) m/e 406 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionH2O extracted with EtOAc
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was crystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-0286d5fd66d64c1382c585dc40e2f807
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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