4-(Chloromethyl)benzoic acid → Ethyl 3-(4-(chloromethyl)benzamido)propanoate

HRID 2039809Notes

Reaction equation

HRID 2039809 reaction equation
[Cl:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.[NH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>>[Cl:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:9])=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 742344-(Chloromethyl)benzoic acidHCID 419889Ethyl 3-aminopropanoate

Product 1

HCID 22502250Ethyl 3-(4-(chloromethyl)benzamido)propanoate

Procedure

Ethyl 3-(4-(chloromethyl)benzamido)propanoate 13f was prepared by coupling 4-(chloromethyl)benzoic acid 24 with ethyl 3-aminopropionate 25 according to the procedure described for the compound 13e in Example 21 (Scheme 8). The compound 13f was isolated as colorless oil in 84% yield (2.26 g). 1H NMR (400 MHz, CDCl3): δ 1.26 (3H, t, J=7.2 Hz); 2.64 (2H, m); 3.72 (2H, m); 4.14 (2H, q, J=7.2 Hz); 4.61 (2H, s); 6.89 (1H, broad s); 7.53 (1H, s); 7.67 (1H, s); 7.70 (1H, s). 7.80 (1H s). MS (ESI): m/z=270.00 (M+H+).

Workup

  1. customEthyl 3-(4-(chloromethyl)benzamido)propanoate 13f was prepared

Sources & evidence

ORD record
ord-ea0011705d2a45bdbb9d6ef4c0cafb0d
Source dataset
uspto-grants-2013_11
Patent number
US08580822B2

Reaction notes

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