Acetic Anhydride → HCID 86690042, compound

HRID 2369338Notes

Reaction equation

[C:1]([C:7]([O:9][CH3:10])=[O:8])#[C:2][C:3]([O:5][CH3:6])=[O:4].[CH2:11]1[C:16]2[NH:17][C:18]3[C:23]([C:15]=2[CH2:14][CH:13](C(O)=O)[NH:12]1)=[CH:22][CH:21]=[CH:20][CH:19]=3.[C:27](OC(=O)C)(=O)[CH3:28]>>[CH3:27][C:28]1[N:12]2[C:13]([CH2:14][C:15]3[C:23]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[NH:17][C:16]=3[CH2:11]2)=[C:2]([C:3]([O:5][CH3:6])=[O:4])[C:1]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

Reactant 3

HCID 7918Acetic Anhydride

HCID 12980Dimethyl acetylenedicarboxylate

HCID 982851,2,3,4-Tetrahydro-Beta-Carboline-3-Carboxylic Acid

Product 1

HCID 86690042HCID 86690042, compound

Conditions

Temperature: 70 °C

Procedure

Dimethyl acetylenedicarboxylate (8.4 g, 59.5 mmol) was added into a mixture of 1,2,3,4-tetrahydro-pyrido[3,4-b]indole-3-carboxylic acid (10 g, 39.6 mmol) in acetic anhydride (70 mL). The reaction mixture was heated at 70° C. with stirring for 2 h and then evaporated in vacuo to dryness. The residue was recrystallized from MeOH to give dimethyl 3-methyl-6,11-dihydro-5H-indolizino[6,7-b]indole-1,2-dicarboxylate, 11.5 g (86%); mp 252-253° C. (lit.20 mp 255-260° C.). 1H NMR (DMSO-d6) δ 2.43 (3H, s, Me), 3.73 (3H, s, COOMe), 3.75 (3H, s, COOMe), 4.16 (2H, s, CH2), 5.21 (2H, s, CH2), 7.02-7.06 (1H, m, ArH), 7.11-7.14 (1H, m, ArH), 7.39 (1H, d, J=8.0 Hz, ArH), 7.52 (1H, d, J=7.8 Hz, ArH), 11.12 (1H, s, exchangeable, NH).

Workup

customevaporated in vacuo to dryness
customThe residue was recrystallized from MeOH

Sources & evidence

ORD record: ord-2743271ce2f94f1fa9f5ea064b4b1b55
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703951B2

Reaction notes

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