Hydrochloric Acid → (2R)-2-amino-3-(3-nitrophenyl)-1-propanol hydrochloride

HRID 47703Notes

Reaction equation

HRID 47703 reaction equation
[OH:1][CH2:2][C@H:3]([NH:14]C(=O)C)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1.[ClH:18]>>[ClH:18].[NH2:14][C@H:3]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1)[CH2:2][OH:1]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 69698954N-[(1R)-2-hydroxy-1-(3-nitrobenzyl)ethyl]acetamide

Product 1

HCID 69885645(2R)-2-amino-3-(3-nitrophenyl)-1-propanol hydrochloride

Conditions

Temperature
100 °C

Procedure

A suspension of 0.98 g of N-[(1R)-2-hydroxy-1-(3-nitrobenzyl)ethyl]acetamide in 10 cm3 of 6N hydrochloric acid is heated at a temperature in the region of 100° C. for 10 hours (dissolution). The reaction medium is concentrated under reduced pressure (2 kPa) at a temperature in the region of 40° C. The residue is taken up in 20 cm3 of diethyl ether and re-evaporated under the same conditions to give beige-colored crystals, which are washed with 3 times 20 cm3 of diethyl ether and then filtered off on a sinter funnel and finally dried in a fume cupboard. 0.92 g of (2R)-2-amino-3-(3-nitrophenyl)-1-propanol hydrochloride is obtained in the form of beige-colored crystals melting at 192° C. [1H NMR spectrum (250 MHz, (CD3)2SO-d6, δ in ppm): 3.06 (limiting AB: 2H); from 3.25 to 3.65 (mt: 3H); 5.45 (t, J=4.5 Hz: 1H); 7.65 (t, J=7 Hz: 1H); 7.79 (broad d, J=7 Hz: 1H); from 8.05 to 8.40 (mt: 5H)].

Workup

  1. dissolution(dissolution)
  2. concentrationThe reaction medium is concentrated under reduced pressure (2 kPa) at a temperature in the region of 40° C
  3. customre-evaporated under the same conditions
  4. customto give beige-colored crystals, which
  5. washare washed with 3 times 20 cm3 of diethyl ether
  6. filtrationfiltered off on a sinter funnel
  7. customfinally dried in a fume cupboard

Sources & evidence

ORD record
ord-4fa3aaf9e3a942f4a4099fcc96b3ca02
Source dataset
uspto-grants-2004_03
Patent number
US06699895B2

Reaction notes

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