Hydrochloric Acid → Ethyl 4-amino-5,6-heptadienoate hydrochloride salt

HRID 979552Notes

Reaction equation

HRID 979552 reaction equation
[NH2:1][CH:2]([CH:8]=[C:9]=[CH2:10])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[ClH:11].[CH2:12](O)[CH3:13]>>[ClH:11].[NH2:1][CH:2]([CH:8]=[C:9]=[CH2:10])[CH2:3][CH2:4][C:5]([O:7][CH2:12][CH3:13])=[O:6]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 102611865,6-Heptadienoic acid, 4-amino-

Product 1

HCID 13920715Ethyl 4-amino-5,6-heptadienoate hydrochloride salt

Procedure

To 4-amino-5,6-heptadienoic acid in anhydrous ethanol at 0° C. was added gaseous HCl. The reaction was left overnight at room temperature and then evacuated to a residue. This was taken in ethyl acetate, decolorized with charcoal, and then crystallization accomplished from ethyl acetate-ether to give the title compound. mp. 81°-83° C.; IR (KBr): 1952, 1710 cm-1. 'H NMR (δD2O): 1.3 (t, 3H, J=6.9 Hz, CH3), 1.9-2.8 (m, 4H, CH2CH2), 3.95 (m, 1H, CHN), 4.2 (q, 2H, J=6.9 Hz, OCH2), 5.0-5.4 (m, 3H H2C=C=CH). Anal. Calcd. for C9H16ClNO2 : C, 52.56, H, 7.84, N, 6.87; Found: C, 52.45, H, 7.95, N, 6.98.

Workup

  1. customevacuated to a residue
  2. customcrystallization

Sources & evidence

ORD record
ord-41aa0a673d2b4e8c959acd2d9c05f16e
Source dataset
uspto-grants-1987_05
Patent number
US04668703

Reaction notes

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