Ammonium Acetate → HCID 90132501, compound

HRID 2275822Notes

Reaction equation

HRID 2275822 reaction equation
O=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[N:5]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:4][CH2:3]1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:29].[Na+]>C(O)C>[NH2:29][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[N:5]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 90113920HCID 90113920, compound

Product 1

HCID 90132501HCID 90132501, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.3 g of tert-butyl 4-oxo-6-(trifluoromethyl)-3,4-dihydroquinoline-1(2H)-carboxylate (Example 159A, 4 mmol, 1 equivalent) were initially charged in 12.6 ml of ethanol, and 4.6 g of ammonium acetate (59.5 mmol, 15 equivalents) and 0.3 g of sodium cyanoborohydride (4.8 mmol, 1.2 equivalents) were added. The reaction mixture was divided and each portion was irradiated in a microwave oven at 130° C. for 1 min. The mixture was then concentrated and the residue was taken up in ethyl acetate and washed with water. The organic phase was dried over sodium sulphate, filtered and concentrated. The crude product obtained was purified on silica gel (mobile phase: dichloromethane/ethyl acetate: 5/1, then dichloromethane/methanol:10/1). This gave 0.84 g (78% of theory) of the title compound.

Workup

  1. customeach portion was irradiated in a microwave oven at 130° C. for 1 min
  2. concentrationThe mixture was then concentrated
  3. washwashed with water
  4. dry with materialThe organic phase was dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3058f1271d9f4206ad6ef8a2569dc1d8
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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