Water → HCID 66958805, compound

HRID 2383219Notes

Reaction equation

HRID 2383219 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]([O:12][C:13]([NH:15][CH2:16][CH2:17][NH2:18])=[O:14])([CH3:11])[CH3:10].[CH2:19]([O:26][C:27]1[CH:36]=[C:35]2[C:30]([C:31](Cl)=[C:32]([N+:37]([O-:39])=[O:38])[CH:33]=[N:34]2)=[CH:29][CH:28]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CN(C=O)C>[C:9]([O:12][C:13](=[O:14])[NH:15][CH2:16][CH2:17][NH:18][C:31]1[C:30]2[C:35](=[CH:36][C:27]([O:26][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:28][CH:29]=2)[N:34]=[CH:33][C:32]=1[N+:37]([O-:39])=[O:38])([CH3:8])([CH3:10])[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 187201N-BOC-ethylenediamineHCID 210757517-(Benzyloxy)-4-chloro-3-nitroquinoline

Product 1

HCID 66958805HCID 66958805, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (58.9 mL, 422.4 mmol, 1.5 eq) and tert-butyl N-(2-aminoethyl) carbamate (54.1 g, 337.9 mmol, 1.2 eq) were added sequentially to a solution of 7-benzyloxy-4-chloro-3-nitroquinoline (88.63 g, 281.6 mmol) in DMF (800 mL) and stirred for 4 hours at ambient temperature. The crude reaction mixture was poured into hot water with continuous stirring to afford bright a yellow precipitate. The yellow solid was filtered and dried under reduced pressure at 65° C. to afford 123.65 g of tert-butyl2-[(7-benzyloxy-3-nitroquinolin-4-yl)amino]ethylcarbamate.

Workup

  1. customThe crude reaction mixture
  2. stirringwith continuous stirring
  3. customto afford bright a yellow precipitate
  4. filtrationThe yellow solid was filtered
  5. customdried under reduced pressure at 65° C.

Sources & evidence

ORD record
ord-a3cfba7a4fcf4012b4e3694250367db3
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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