Hydrochloric Acid → HCID 53408381, compound

HRID 2383669Notes

Reaction equation

HRID 2383669 reaction equation
FC(F)(F)S([O-])(=O)=O.[Br:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[N+:15]([CH3:20])[CH:14]=[CH:13]2.CC1C(Br)=C(O)C(Br)=CC=1C1(C2C=C(Br)C(O)=C(Br)C=2C)OS(=O)(=O)C2C=CC=CC1=2.[BH4-].[Na+].Cl.[OH-].[Na+]>CO.C(O)(=O)C.O>[Br:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH2:16][N:15]([CH3:20])[CH2:14][CH2:13]2

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6451Bromocresol GreenHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 86658834HCID 86658834, compound

Product 1

HCID 53408381HCID 53408381, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 6-bromo-2-methylisoquinolinium trifluoromethanesulfonate (371 mg, 1 mmol) in methanol (10 mL) was added bromocresol green indicator. Sodium borohydride (93 mg, 2.5 mmol) was added and the reaction was stirred at rt. HCl in acetic acid (1M) was added periodically to maintain a yellow color. After 1 h, water (50 mL) was added and the solution was basified with NaOH (1M), extracted into CH2Cl2 (100 mL), dried over MgSO4 and concentrated to give the title compound as a white solid (200 mg, 99%). 1H NMR (400 MHz, CDCl3) δ 7.29-7.17 (m, 2H), 6.88 (d, J=8.0 Hz, 1H), 3.51 (s, 2H), 2.93-2.82 (m, 2H), 2.65 (t, J=5.8 Hz, 2H), 2.45 (s, 3H).

Workup

  1. temperatureto maintain a yellow color
  2. extractionextracted into CH2Cl2 (100 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b7055cbbd7e24f54a57fba1a7925c424
Source dataset
uspto-grants-2012_09
Patent number
US08263596B2

Reaction notes

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