Sodium borohydride → HCID 67491614, compound

HRID 1920683Notes

Reaction equation

HRID 1920683 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[C:5]([CH2:16][O:17][CH3:18])=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[C:11]([CH:14]=[O:15])[CH:10]=[CH:9]2>C(O)C>[Cl:3][C:4]1[C:5]([CH2:16][O:17][CH3:18])=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[C:11]([CH2:14][OH:15])[CH:10]=[CH:9]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86639217HCID 86639217, compound

Product 1

HCID 67491614HCID 67491614, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Referring to FIG. 20, NaBH4 (0.0028 g, 0.074 mmol) was added to a solution of 9c (0.0397 g, 0.158 mmol) in ethanol (4 mL). The mixture was stirred for 20 min. The solvent was evaporated, and the resulting solid residue was dissolved in chloroform, then washed with water (×2) followed by brine, dried over MgSO4, and concentrated to afford 10c (0.0396 g, 0.156 mmol, 99%) as a white, crystalline solid (mp 84-87° C.): 1H NMR (CDCl3) δ 8.09 (1H, d, J=8.4 Hz), 7.71 (1H, d, J=8.8 Hz), 7.52 (1H, d, J=9.2 Hz), 7.24 (1H, d, J=8.4 Hz), 5.41 (2H, s), 4.94 (2H, s) 3.58 (3H, s); 13C NMR (CDCl3) δ 160.3, 154.2, 144.1, 137.2, 127.0, 124.4, 120.0, 117.4, 117.2, 95.7, 64.4, 56.8; FTIR (neat) 3342, 2925, 1615, 1155, 1005, 835, 781 cm−1; MS (ESI) m/z calculated for (C12H12ClNO3+H)+ 254 (35Cl) and 256 (37Cl), found 254 (35Cl) and 256 (37Cl); HRMS (ESI) m/z calculated for (C12H12ClNO3+H)+ 254.0584 (35Cl) and 256.0554 (37Cl), found 254.0577 (35Cl) and 256.0546 (37Cl).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe resulting solid residue was dissolved in chloroform
  3. washwashed with water (×2)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8eeff313da784039b2de21a0e0b0f50a
Source dataset
uspto-grants-2012_05
Patent number
US08173620B2

Reaction notes

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