Water → HCID 66958805, compound

HRID 599460Notes

Reaction equation

HRID 599460 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[CH2:12]([O:19][C:20]1[CH:29]=[C:28]2[C:23]([C:24](Cl)=[C:25]([N+:30]([O-:32])=[O:31])[CH:26]=[N:27]2)=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.O>CN(C=O)C>[CH2:12]([O:19][C:20]1[CH:29]=[C:28]2[C:23]([C:24]([NH:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:10])[CH3:9])=[C:25]([N+:30]([O-:32])=[O:31])[CH:26]=[N:27]2)=[CH:22][CH:21]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

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

Product 1

HCID 66958805HCID 66958805, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl 2-aminoethylcarbamate (54.1 g, 338 mmol) was added to a stirred solution of 7-benzyloxy-4-chloro-3-nitroquinoline (88.6 g, 282 mmol) and triethylamine (58.9 mL, 422 mmol) in DMF (800 mL) at room temperature. The reaction mixture was stirred for 4 hours, then was poured onto stirred hot water in a beaker to precipitate a yellow solid that was isolated by filtration and dried under vacuum at 65° C. to yield 123.7 g of tert-butyl 2-{[7-(benzyloxy)-3-nitroquinolin-4-yl]amino}ethylcarbamate.

Workup

  1. additionwas poured
  2. customto precipitate a yellow solid
  3. customthat was isolated by filtration
  4. customdried under vacuum at 65° C.

Sources & evidence

ORD record
ord-f046c3d72a184507a685ba4c1ef0bd72
Source dataset
uspto-grants-2011_03
Patent number
US07897767B2

Reaction notes

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