Ammonium Chloride → HCID 58188278, compound

HRID 1845291Notes

Reaction equation

HRID 1845291 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([C:18](OC)=[O:19])[CH:11]=[C:12]([CH:17]=2)[C:13]([O:15][CH3:16])=[O:14])=[N:6][CH:7]=1.[BH4-].[Na+].[NH4+].[Cl-]>CO>[OH:19][CH2:18][C:10]1[CH:11]=[C:12]([CH:17]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=2)[CH:9]=1)[C:13]([O:15][CH3:16])=[O:14]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 58188082HCID 58188082, compound

Product 1

HCID 58188278HCID 58188278, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of dimethyl 5-(5-methylpyridin-2-yl)isophthalate (1.78 g, 5.93 mmol) in methanol (100 mL) was added sodium tetrahydroborate (2.0 g, 0.053 mol) at 0° C. After 3 h, the reaction was treated with sat. aq. NH4Cl and the volatiles were removed in vacuo. The residue was dissloved in water, basified to pH=9 by addition of NaHCO3, and then extracted with CH2Cl2 (70 mL×3). The combined organic layers were dried over anhydrous MgSO4 and concentrated. The residue was purified by flash chromatography to afford the title compound.

Workup

  1. customthe volatiles were removed in vacuo
  2. additionbasified to pH=9 by addition of NaHCO3
  3. extractionextracted with CH2Cl2 (70 mL×3)
  4. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-f6f962850778497c99a741de12813f91
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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