Hydrochloric Acid → HCID 15295564, compound

HRID 1720143Notes

Reaction equation

HRID 1720143 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][C:18]=1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[O:8])([O-])=O.Cl.[OH-].[Na+]>>[NH2:1][C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][C:18]=1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[O:8]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15295563HCID 15295563, compound

Product 1

HCID 15295564HCID 15295564, compoundYield 0.1%

Procedure

5-(3-nitro-4-n-heptylbenzoyl)pentanoic acid (0.7 g; 2.1 mole) is stirred overnight at room temperature in a mixture of stannous chloride (1.35 g) and concentrated hydrochloric acid (1.8 ml). The reaction product is mixed with excess 1M sodium hydroxide and washed with ether. The aqueous phase is acidified to pH 5 with dilute hydrochloric acid. The precipitate is collected and recrystallized from aqueous ethanol to give 5-(3-amino-4-n-heptylbenzoyl)pentanoic acid (0.46 g) as a cream colored crystalline solid, m.p. 100°-102° C. The structure is confirmed by NMR and IR spectroscopy.

Workup

  1. washwashed with ether
  2. customThe precipitate is collected
  3. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-36d69e7d55504895a15d8245f806930d
Source dataset
uspto-grants-1996_04
Patent number
US05504244

Reaction notes

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