Ethanol → 8-Chloro-5,10-dihydro-indeno[1,2-b]indole-1-carboxylic acid ethyl ester

HRID 1595470Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[C:11]4[CH:12]=[CH:13][CH:14]=[C:15]([C:18]([OH:20])=[O:19])[C:16]=4[CH2:17][C:5]=3[C:4]=2[CH:3]=1.S(=O)(=O)(O)O.[CH2:26](O)[CH3:27]>>[CH2:26]([O:19][C:18]([C:15]1[C:16]2[CH2:17][C:5]3[C:4]4[CH:3]=[C:2]([Cl:1])[CH:10]=[CH:9][C:8]=4[NH:7][C:6]=3[C:11]=2[CH:12]=[CH:13][CH:14]=1)=[O:20])[CH3:27]

Participants

Reactant 3

HCID 702Ethanol

HCID 1118Sulfuric Acid

HCID 224628258-Chloro-5,10-dihydro-indeno[1,2-b]indole-1-carboxylic acid

Product 1

HCID 543584048-Chloro-5,10-dihydro-indeno[1,2-b]indole-1-carboxylic acid ethyl ester

Procedure

The product of Example 20 was converted to its ethyl ester by treatment with sulfuric acid in ethanol to give the title compound as an off-white solid: mp 202-204° C.; 1H NMR (DMSO-d6,): δ 1.39 (t, 3H), 4.00 (s, 2H), 4.38 (q, 2H), 7.11 (d, 1H), 7.48 (d, 1H), 7.52 (t, 1H), 7.67 (s, 1H), 7.79-7.84 (m, 2H), 11.86 (s, 1H); MS [EI, m/z]: 311 [M]+.

Sources & evidence

ORD record: ord-ca43f1bcaef4490095b4da545e0b79bd
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06288099B1

Reaction notes

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