Hydrochloric Acid → HCID 68497066, compound

HRID 1944203Notes

Reaction equation

HRID 1944203 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][C:8]([CH3:14])([CH3:13])[N:9]=[CH:10]2)=[CH:5][C:4]=1[OH:15].[BH4-].[Na+].O.Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][C:8]([CH3:13])([CH3:14])[NH:9][CH2:10]2)=[CH:5][C:4]=1[OH:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 136346362HCID 136346362, compound

Product 1

HCID 68497066HCID 68497066, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 223 (1.67 mg, 8.2 mmol) in ethanol (30 ml) at 0° C. was added sodium borohydride (618 mg, 16.3 mmol). The reaction mixture was stirred at rt for 3 h. Water (50 ml) was added and the aqueous layer neutralised (2M HCl) and extracted with ethyl acetate (3×60 ml). The combined organic layers were washed with brine (30 ml), dried (MgSO4) and concentrated in vacuo to afford the title compound (1.34 mg, 80%) as a white solid. mp=170-173° C. 1H NMR (270 MHz; DMSO-d6) 1.04 (6H, s, 2×CH3), 2.42 (2H, s, CH2), 3.70 (3H, s, OCH3), 3.72 (2H, s, CH2), 6.43 (1H, s, CH), 6.54 (1H, s, CH), 8.60 (1H, brs, NH). LC/MS (ES+) tr=1.19 min, m/z 208.23 (M++H). HRMS (ES+) calcd. for C12H17NO2 (M++H) 208.1332, found 208.1322.

Workup

  1. extractionextracted with ethyl acetate (3×60 ml)
  2. washThe combined organic layers were washed with brine (30 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7bfc004f322e4c3da7cd5f4ce47091ef
Source dataset
uspto-grants-2013_03
Patent number
US08394825B2

Reaction notes

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