Acetic Anhydride → Ethyl 2-(acetylamino)-3-(3-nitrophenyl)propanoate

HRID 1280605

Reaction equation

HRID 1280605 reaction equation
[NH2:1][CH:2]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:18](OC(=O)C)(=[O:20])[CH3:19]>>[C:18]([NH:1][CH:2]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4])(=[O:20])[CH3:19]

Participants

3

Reactant 2

HCID 7918Acetic Anhydride2×HCID 5040514Ethyl 2-amino-3-(3-nitrophenyl)propanoate

Product 1

HCID 22292739Ethyl 2-(acetylamino)-3-(3-nitrophenyl)propanoate

Conditions

Temperature
0 °C

Procedure

9.52 cm3 of acetic anhydride are added dropwise to 12 g of ethyl 2-amino-3-(3-nitrophenyl)propanoate at a temperature in the region of 0° C. After stirring at 0° C. for 1 hour, the mixture sets to a solid. 10 cm3 of acetic anhydride are then added and stirring is continued at 0° C. for a further 1 hour. The precipitate is filtered off on a sinter funnel, washed with 3 times 25 cm3 of water and dried in a fume cupboard and then in an oven under vacuum (10 Pa) at a temperature in the region of 50° C. 12 g of ethyl 2-(acetylamino)-3-(3-nitrophenyl)propanoate are obtained in the form of white crystals melting at 91° C. 1H NMR spectrum (250 MHz, (CD3)2SO-d6, δ in ppm): 1.14 (t, J=7 Hz: 3H); 1.80 (s: 3H); 3.04 (dd, J=14 and 9 Hz: 1H); 3.18 (t, J=14 and 4 Hz: 1H); 4.08 (q, J=7 Hz: 2H); 4.52 (mt: 1H); 7.61 (broad t, J=8 Hz: 1H); 7.72 (broad d, J=8 Hz: 1H); 8.12 (mt: 2H); 8.42 (d, J=8.5 Hz: 1H).

Workup

  1. stirringstirring
  2. waitis continued at 0° C. for a further 1 hour
  3. filtrationThe precipitate is filtered off on a sinter funnel
  4. washwashed with 3 times 25 cm3 of water
  5. customdried in a fume cupboard
  6. customin the region of 50° C

Sources & evidence

ORD record
ord-88e9569f3912494ab818dc3c25e0605e
Source dataset
uspto-grants-2002_09
Patent number
US06451821B1

Linked notes

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