Benzenamine, 3-ethynyl- → Methyl 3-(4-((3-aminophenyl)ethynyl)phenyl)propanoate

HRID 2042985Notes

Reaction equation

HRID 2042985 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[C:14]([C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19])#[CH:15]>>[NH2:19][C:18]1[CH:17]=[C:16]([C:14]#[C:15][C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=2)[CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 104682Benzenamine, 3-ethynyl-HCID 554150Methyl 3-(4-iodophenyl)propanoate

Product 1

HCID 58319116Methyl 3-(4-((3-aminophenyl)ethynyl)phenyl)propanoate

Procedure

The title compound was prepared from methyl 3-(4-iodophenyl)propanoate (100 mg, 0.34 mmol) and 3-ethynylaniline (0.04 mL, 0.38 mmol) according to the general procedure IC to give 89 mg (93%) of an orange solid after purification by flash chromatography (SiO2, EtOAc/hexanes, 1:3). Rf: 0.35 (EtOAc:hexanes, 1:1); 1HNMR (CDCl3) δ 7.44-7.42 (m, 2H), 7.18-7.09 (m, 3H), 6.93-6.91 (m, 1H), 6.83 (s, 1H), 6.66-6.63 (m, 1H), 3.66 (s, 3H), 2.98-2.93 (t, 2H, J=7.8 Hz), 2.65-2.60 (t, 2H, J=7.8 Hz); 13CNMR (CDCl3) δ 173.1, 146.3, 140.7, 131.7, 129.2, 128.3, 124.0, 122.0, 121.3, 117.7, 115.2, 89.3, 88.6, 51.6, 35.4, 30.8; EI-MS m/z 279 (M+).

Sources & evidence

ORD record
ord-fa8284288fca48418c329d60022a0897
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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