Sulfuric Acid → HCID 44549271, compound

HRID 2238385Notes

Reaction equation

[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[C:15]([C:16]#[N:17])[C:9]=3[CH:8]=[CH:7][C:6]=2[N:5]([C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[CH2:4]1.[OH:24]S(O)(=O)=O>>[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[C:15]([C:16]([NH2:17])=[O:24])[C:9]=3[CH:8]=[CH:7][C:6]=2[N:5]([C:18](=[O:23])[C:19]([F:22])([F:20])[F:21])[CH2:4]1

Participants

Reactant 2

HCID 1118Sulfuric Acid

HCID 44549270HCID 44549270, compound

Product 1

HCID 44549271HCID 44549271, compoundYield 78%

Conditions

Temperature: 70 °C

Procedure

Solid 126 (500 mg, 1.48 mmol), was added to 90% H2SO4 (5 μL) and heated to 70° C. for 1 h. After cooling to room temperature, the mixture was poured into ice-water and extracted with EtOAc (3×50 mL). The extracts were dried and concentrated under reduced pressure. Chromatography of the residue on silica gel (EtOAc/petroleum ether, from 1:1 to 1:0) gave 1-(chloromethyl)-3-(trifluoroacetyl)-1,2-dihydro-3H-benzo[e]indole-6-carboxamide (128) (410 mg, 78%) as a white solid: mp (EtOAc/petroleum ether) 190-193° C.; 1H NMR (CDCl3) δ 8.54-8.45 (m, 2H), 7.89 (d, J=5.8 Hz, 1H), 7.69 (dd, J=7.1, 1.1 Hz, 1H), 7.59 (dd, J=8.4, 7.1 Hz, 1H), 5.91 (br, 2H), 4.69-4.61 (m, 1H), 4.48-4.40 (m, 1H), 4.25-4.17 (m, 1H), 3.97-3.89 (m, 1H), 3.58-3.50 (m, 1H; 13C NMR δ 170.7, 153.8 (q, JC-F 38.0 Hz), 140.5, 134.6, 129.7, 128.6, 126.5, 125.6, 125.4, 124.8, 118.4, 115.4 (q, JC-F 288 Hz), 53.4, 45.4, 43.0. Anal. (C16H12ClF3N2O2) C, H, N, Cl.

Workup

temperatureAfter cooling to room temperature
extractionextracted with EtOAc (3×50 mL)
customThe extracts were dried
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-c02889dd18d549eea4a215e139f0d931
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07718688B2

Reaction notes

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