2-Amino-3-chlorobenzoic acid → HCID 89837820, compound

HRID 1749008Notes

Reaction equation

HRID 1749008 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=O)[C:3]=1[NH2:11].CC(=O)O[CH2:15][CH3:16].[CH3:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]2[C:3]=1[N:11]=[C:3]([CH2:2][CH3:10])[N:11]([CH2:18][CH2:19][C:20]1[CH:16]=[CH:15][CH:23]=[CH:22][CH:21]=1)[C:5]2=[O:7]

Participants

3

Reactant 2

HCID 808072-Amino-3-chlorobenzoic acidHCID 21226206Ethyl acetate hexane

Product 1

HCID 89837820HCID 89837820, compound

Procedure

The title compound was prepared using the procedure described above of the step 1 of example 1 from 3-chloroanthranilic acid (5 g, 29.14 mmol) to give white needle crystal (4.3 g, 47.2%), Rf=0.53 (EA/Hexane=1:2); 1H NMR (400 MHz, DMSO-d6) δ 1.24 (t, J=7.2 Hz, 3H), 2.79 (q, J=7.2 Hz, 2H), 2.94 (t, J=7.6 Hz, 2H), 4.20 (t, J=7.6 Hz, 2H), 7.20-7.31 (m, 5H), 7.41 (dd, J=8.0, 7.6 Hz, 1H), 7.89 (d, J=17.6 Hz, 1H), 8.05 (d, J=8.0 Hz, 1H); 13C NMR (100 MHz, DMSO-d6) δ 10.5, 27.1, 33.5, 44.7, 121.4, 125.2, 126.4, 126.5, 128.5, 128.7, 130.3, 134.1, 138.1, 143.1, 158.7, 160.5; Anal. (C18H17ClN2O) C, H, N. Calcd: 69.12, 5.48, 8.96. Found: 69.11, 5.38, 8.94.

Sources & evidence

ORD record
ord-99f80697ea2c4693907c20a2c36972b5
Source dataset
uspto-grants-2015_10
Patent number
US09155739B2

Reaction notes

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