Hydrochloric Acid → HCID 53408381, compound

HRID 1466350Notes

Reaction equation

HRID 1466350 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 (IM) 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 MgSO4and 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. customdried over MgSO4and
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2d0e00b6e3e04d00b4c66f532578b603
Source dataset
uspto-grants-2015_04
Patent number
US08999968B2

Reaction notes

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