Ammonium Hydroxide → Oxane-4-carboxamide

HRID 540802

Reaction equation

HRID 540802 reaction equation
C(OC1C([N+]([O-])=O)=C(N)C2C(=CC=CC=2)[N:10]=1)C1C=CC=CC=1.C(OC1C([N+]([O-])=O)=C(Cl)C2C(=CC=CC=2)N=1)C1C=CC=CC=1.[O:45]1[CH2:50][CH2:49][CH:48]([C:51]([O:53]C)=O)[CH2:47][CH2:46]1.[OH-].[NH4+]>C(N(CC)CC)C.CO.ClCCl>[O:45]1[CH2:50][CH2:49][CH:48]([C:51]([NH2:10])=[O:53])[CH2:47][CH2:46]1

Participants

8

Reactant 4

HCID 14923Ammonium HydroxideHCID 27735202H-Pyran-4-carboxylic acid, tetrahydro-, methyl esterHCID 21075762Benzyloxy-4-chloro-3-nitroquinolineHCID 66649911Benzyloxy-3-nitroquinolin-4-amine

Product 1

HCID 13197203Oxane-4-carboxamide

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

In step (5) of Reaction Scheme I, a benzyloxy-4-chloro-3-nitroquinoline of Formula XIX is treated with an amine of Formula R1—NH2 to provide a benzyloxy-3-nitroquinolin-4-amine of Formula XX. The reaction is conveniently carried out by adding the amine of Formula R1—NH2 to a solution of the benzyloxy-4-chloro-3-nitroquinoline of Formula XIX in a suitable solvent such as dichloromethane or methanol in the presence of a tertiary amine such as triethylamine. The reaction can be carried out at ambient temperature or at an elevated temperature such as, for example, the reflux temperature of the solvent. The reaction product can be isolated using conventional methods. Several mines of Formula R1—NH2 are commercially available; others can be prepared by known synthetic methods. For example, methyl tetrahydro-2H-pyran-4-carboxylate treated with ammonium hydroxide to form tetrahydro-2H-pyran-4-carboxamide, which can then be reduced with lithium aluminum hydride to provide tetrahydro-2H-pyran-4-ylmethylamine.

Workup

  1. customThe reaction
  2. customcan be carried out at ambient temperature or at an elevated temperature
  3. customThe reaction product can be isolated
  4. customothers can be prepared

Sources & evidence

ORD record
ord-ce9fce475629448ab676fa3dcd87db44
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Linked notes

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