Ammonia → HCID 18973853, compound

HRID 2395056Notes

Reaction equation

HRID 2395056 reaction equation
[CH2:1]([O:8][C:9]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][C:10]=1[CH2:11][CH2:12][C:13]1[N:18]=[C:17]([Cl:19])[C:16]([C:20](OC)=[O:21])=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:29]>C(O)C>[CH2:1]([O:8][C:9]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][C:10]=1[CH2:11][CH2:12][C:13]1[N:18]=[C:17]([Cl:19])[C:16]([C:20]([NH2:29])=[O:21])=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 18974085HCID 18974085, compound

Product 1

HCID 18973853HCID 18973853, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 6-[2-benzyloxy-5-bromophenethyl]-2-chloro-3-pyridinecarboxylate (2.0 g) in ethanol (60 ml) saturated with ammonia was heated at 177° C. under pressure for 6 hours. The solvent was evaporated and the residue subjected to chromatography on silica gel (7734). Two products were isolated. The first was eluted with 2.5% ethyl acetate/CH2Cl2 and the second with 5% MeOH/CH2Cl2. The first product was identified as a mixture of the methyl and ethyl esters of 6-[2-benzyloxy-5-bromophenethyl]-2-amino-3-pyridinecarboxylic aicd (0.3 g). The second produce was identified as the title compound (0.6 g) mpt. 142°-144° C.

Workup

  1. customThe solvent was evaporated
  2. customTwo products were isolated
  3. washThe first was eluted with 2.5% ethyl acetate/CH2Cl2
  4. additionThe first product was identified as a mixture of the methyl and ethyl esters of 6-[2-benzyloxy-5-bromophenethyl]-2-amino-3-pyridinecarboxylic aicd (0.3 g)
  5. customThe second produce

Sources & evidence

ORD record
ord-bbad0905639b4d2a9e40beb98b6b5975
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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