2-Chloro-4-trifluoromethylaniline → HCID 86709744, compound

HRID 2174610Notes

Reaction equation

HRID 2174610 reaction equation
[C:1]1([C@@H:7]2[C:9]3([CH2:13][CH2:12][CH2:11][CH2:10]3)[C@H:8]2[C:14]([OH:16])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:17][C:18]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:19]=1[NH2:28]>>[C:1]1([C@@H:7]2[C:9]3([CH2:10][CH2:11][CH2:12][CH2:13]3)[C@H:8]2[C:14]([NH:28][C:19]2[CH:20]=[CH:21][C:22]([C:24]([F:25])([F:26])[F:27])=[CH:23][C:18]=2[Cl:17])=[O:16])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 1620012-Chloro-4-trifluoromethylanilineHCID 86709739HCID 86709739, compound

Product 1

HCID 86709744HCID 86709744, compoundYield 57%

Procedure

trans-2-Phenylspiro[2.4]heptane-1-carboxylic acid (300 mg, 1.39 mmol) and 2-chloro-4-trifluoromethyl-phenylamine (272 mg, 1.39 mmol) were reacted as described under General Procedure D to furnish the title compound (312 mg, 57%) as a white solid. 1H NMR (300 MHz, d6-DMSO) δ 9.91 (s, 1H), 8.20 (d, J=8.5 Hz, 1H), 7.89 (d, J=1.6 Hz, 1H), 7.67 (d, J=8.5, 1.6 Hz, 1H), 7.31 (t, J=7.3 Hz, 2H), 7.22-7.16 (m, 3H), 2.80 (d, J=5.7 Hz, 1H), 2.70 (d, J=5.7 Hz, 1H), 1.82-1.73 (m, 2H), 1.66-1.42 (m, 5H), 1.29-1.10 (m, 1H). mp 131-133° C. ESIMS m/z [M+H]+ 394.3.

Sources & evidence

ORD record
ord-a9e21ee111b1410d8eef8c6332529ea1
Source dataset
uspto-grants-2015_06
Patent number
US09062013B2

Reaction notes

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