Hydrochloric Acid → HCID 71546348, compound

HRID 707198Notes

Reaction equation

HRID 707198 reaction equation
[CH3:1][N:2]1[C:11]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=3[C:18](=[O:19])[C:10]=2[C:9]2[C:4](=[CH:5][C:6]([NH:20][C:21](=[O:27])[CH2:22][C:23]([O:25]C)=[O:24])=[CH:7][CH:8]=2)[C:3]1=[O:28].[OH-].[Na+].Cl>CO.CN(C)C=O.O.C(Cl)(Cl)Cl>[CH3:1][N:2]1[C:11]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=3[C:18](=[O:19])[C:10]=2[C:9]2[C:4](=[CH:5][C:6]([NH:20][C:21](=[O:27])[CH2:22][C:23]([OH:25])=[O:24])=[CH:7][CH:8]=2)[C:3]1=[O:28]

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 71546176HCID 71546176, compound

Product 1

HCID 71546348HCID 71546348, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

Methyl 3-[(6-methyl-5,11-dioxo-6,11-dihydro-5H-indeno[1,2-c]isoquinolin-3-yl)amino]-3-oxopropanoate (10, 158 mg, 0.42 mmol) was dissolved in methanol (20 mL) and dimethylformamide (2 mL). A solution of sodium hydroxide (103 mg) in water (2 mL) was added dropwise and the reaction mixture was stirred at room temperature for 24 h. Concentrated hydrochloric acid (1 mL) was added and the solution diluted with chloroform (30 mL). A dark-red precipitated was formed between the two phases. The solid was filtered and the organic and water layers discarded. The solid was washed with water (10 mL) and ether (2×10 mL). The solid was dried and compound 15 was obtained as a reddish-brown solid (93 mg, 61%): mp 262° C. (dec). IR (KBr) 3447, 3323, 1731, 1695, 1573, 1529, 1433, 1317, 1195, 1054, 899, 763 cm−1; 1H NMR (300 MHz, DMSO-d6) δ 10.5 (s, 1H), 8.45 (s, 1H), 8.31 (d, J=8.6 Hz, 1H), 7.80 (d, J=7.0 Hz, 1H), 7.46-7.38 (m, 3H), 3.86 (s, 3H), 3.39 (s, 2H); 13C NMR (125 MHz, DMSO-d6) δ 190.1, 169.5, 165.1, 162.4, 155.7, 138.1, 137.5, 134.5, 133.8, 131.2, 127.6, 125.7, 124.1, 123.6, 122.7, 117.0, 116.9, 106.9, 44.4, 32.4; MALDIMS m/z (rel intensity) 363 (MH+, 100); ESIMS (m/z, relative intensity) 361 [(M-H+)−], 100); HRESIMS calcd for C20H14N2O5 361.0824 [(M-H+)−]. found 361.0828 [(M-H+)−]; negative ion; HPLC purity: 99.4% (MeOH, 100), 98.6% (MeOH—H2O, 95:5).

Workup

  1. customA dark-red precipitated
  2. customwas formed between the two phases
  3. filtrationThe solid was filtered
  4. washThe solid was washed with water (10 mL) and ether (2×10 mL)
  5. customThe solid was dried

Sources & evidence

ORD record
ord-9af6194639fb4f41ad902333881cfec6
Source dataset
uspto-grants-2015_11
Patent number
US09175002B2

Reaction notes

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