Chloroacetyl chloride → HCID 12818625, compound

HRID 1703130Notes

Reaction equation

HRID 1703130 reaction equation
C([O:3][C:4]([C:6]1[C:7](=[O:20])[N:8]([CH2:17][CH:18]=[CH2:19])[C:9]2[C:14]([C:15]=1[NH2:16])=[CH:13][CH:12]=[CH:11][N:10]=2)=[O:5])C.[Cl:21][CH2:22][C:23](Cl)=[O:24]>>[Cl:21][CH2:22][C:23]([NH:16][C:15]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:17][CH:18]=[CH2:19])[C:7](=[O:20])[C:6]=1[C:4]([OH:3])=[O:5])=[O:24]

Participants

3

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 12818621HCID 12818621, compound

Product 1

HCID 12818625HCID 12818625, compound

Procedure

A stirred mixture of 4 g. of 1-allyl-4-amino-1,2-dihydro-2-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester in 30 ml. of chloroacetyl chloride was heated under reflux for 1 hour. The chloroacetyl chloride was evaporated in a rotary evaporator and the residue was triturated with 20 ml. of ethyl acetate. The insoluble material was collected and was recrystallized from ethyl acetate to give 1.2 g. of product, m.p. 145°-148° C.

Workup

  1. additionA stirred mixture of 4 g
  2. temperatureunder reflux for 1 hour
  3. customThe chloroacetyl chloride was evaporated in a rotary evaporator
  4. customthe residue was triturated with 20 ml
  5. customThe insoluble material was collected
  6. customwas recrystallized from ethyl acetate
  7. customto give 1.2 g

Sources & evidence

ORD record
ord-97914c6097204e148e56ec22833d3b7c
Source dataset
uspto-grants-1982_09
Patent number
US04350817

Reaction notes

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