p-Toluenesulfonic acid monohydrate → Ammonia

HRID 591685Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([O:13][CH3:14])[C:3]=1[C:4]([NH2:6])=[O:5].[N:15]1([CH2:20][C:21]2[NH:22][C:23]3[C:28]([CH:29]=2)=[CH:27][C:26]([CH:30]=O)=[CH:25][CH:24]=3)[CH2:19][CH2:18][CH2:17][CH2:16]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.S(=O)(O)[O-].[Na+]>CN(C)C(=O)C.C([O-])([O-])=O.[Na+].[Na+]>[NH3:1].[CH3:14][O:13][C:7]1[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=[C:2]2[C:3]=1[C:4](=[O:5])[NH:6][C:30]([C:26]1[CH:27]=[C:28]3[C:23](=[CH:24][CH:25]=1)[NH:22][C:21]([CH2:20][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)=[CH:29]3)=[N:1]2

Participants

Conditions

Temperature: 115 °C

Procedure

A mixture of 2-amino-4,6-dimethoxy-benzamide (0.20 g, 1.0 mmol), crude 2-pyrrolidin-1-ylmethyl-1H-indole-5-carbaldehyde (0.23 g, 1.0 mmol), p-toluenesulfonic acid monohydrate (0.38 g, 2.0 mmol), and sodium bisulfite (0.42 g, 4.0 mmol) in N,N-dimethylacetamide (5 mL) was stirred at 115° C. under N2 for 17 hours and cooled to room temperature. The mixture was diluted with saturated Na2CO3 aqueous solution and concentrated to dryness under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with CH2Cl2:7.0 M NH3 in MeOH (95:5), to afford the title compound as a yellow solid. Yield: 87 mg (22%). MP 168-169.5° C. (decomposition). 1H NMR (400 MHz, CDCl3): δ 9.05 (s, 1H), 8.22 (s, 1H), 7.85 (d, 1H), 7.43 (d, 1H), 6.84 (s, 1H), 6.45 (s, 1H), 6.43 (s, 1H), 3.96 (s, 3H), 3.92 (s, 3H), 3.81 (s, 2H), 2.57 (m, 4H), 1.81 (m, 4H).

Workup

temperaturecooled to room temperature
concentrationconcentrated to dryness under reduced pressure
customThe residue was purified by column chromatography on silica gel
washeluting with CH2Cl2

Sources & evidence

ORD record: ord-950d39e968914583aa69ec3d73eadc11
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238640B2

Reaction notes

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