Dimethylformamide → Tert-butyl 6-bromo-8-nitro-2-oxo-1,2,3,4-tetrahydroquinolin-3-ylcarbamate

HRID 2070123Notes

Reaction equation

HRID 2070123 reaction equation
Cl.[NH2:2][CH:3]1[CH2:12][C:11]2[C:6](=[C:7]([N+:14]([O-:16])=[O:15])[CH:8]=[C:9]([Br:13])[CH:10]=2)[NH:5][C:4]1=[O:17].CN(C=O)C.C(N(CC)CC)C.[C:30](=O)([O:36]C(C)(C)C)[O:31][C:32]([CH3:35])([CH3:34])[CH3:33]>O>[Br:13][C:9]1[CH:10]=[C:11]2[C:6](=[C:7]([N+:14]([O-:16])=[O:15])[CH:8]=1)[NH:5][C:4](=[O:17])[CH:3]([NH:2][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:12]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 684113113-amino-6-bromo-8-nitro-3,4-dihydroquinolin-2(1H)-one hydrochloride

Product 1

HCID 59620339Tert-butyl 6-bromo-8-nitro-2-oxo-1,2,3,4-tetrahydroquinolin-3-ylcarbamateYield 92.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Amino-6-bromo-8-nitro-3,4-dihydroquinolin-2(1H)-one hydrochloride (610 g) was added to N,N-dimethylformaldehyde (3 L), and triethylamine (554 mL) was added dropwise to the mixture under cooling on ice. Subsequently, di-tert-butyl carbonate (454 g) was added thereto, and the resultant mixture was stirred at room temperature for 30 minutes. Water (3 L) was added to the reaction mixture, and stirring was performed for 30 minutes under cooling on ice. The precipitates were recovered through filtration and washed sequentially with water and diisopropyl ether. The thus-obtained solid was dried, whereby the title compound (674 g) was yielded as a powdery compound.

Workup

  1. additionwas added dropwise to the mixture
  2. temperatureunder cooling on ice
  3. temperatureunder cooling on ice
  4. filtrationThe precipitates were recovered through filtration
  5. washwashed sequentially with water and diisopropyl ether
  6. customThe thus-obtained solid was dried

Sources & evidence

ORD record
ord-9f40415666314bb682ba8d96f2f1818f
Source dataset
uspto-grants-2012_10
Patent number
US08299255B2

Reaction notes

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