Methylhydrazine → HCID 67468204, compound

HRID 1908007Notes

Reaction equation

[ClH:1].C(O/[CH:5]=[C:6]1\[C:7](=O)[C:8]2[C:13]([O:14][C:15]3\1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[CH:12][CH:11]=[CH:10][CH:9]=2)C.[CH3:22][NH:23][NH2:24]>C(O)C>[ClH:1].[CH3:22][N:23]1[CH:5]=[C:6]2[C:15]3([O:14][C:13]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=4[C:7]2=[N:24]1)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3

Participants

Conditions

Temperature: 70 °C

Procedure

(Z)-3-(Ethoxymethylene)spiro[chroman-2,4′-piperidin]-4-one hydrochloride (2.46 g, 7.94 mmol) in ethanol (24.6 mL) was treated with methylhydrazine (423 μL, 7.94 mmol). The reaction mixture was heated at 70° C. for 1 h and then at 100° C. for 10 min. The mixture was allowed to cool to room temperature overnight. The yellow solid was filtered off and was washed with ethanol to give 2-methylspiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]hydrochloride (1.20 g, 74%). ESI-MS m/z calc. 255.1. found 256.3 (M+1)+; Retention time: 0.65 minutes. 1H NMR (400 MHz, DMSO) δ 9.01 (s, 2H), 7.75 (s, 1H), 7.61 (dd, J=7.5, 1.2 Hz, 1H), 7.28-7.20 (m, 1H), 7.10-6.99 (m, 2H), 3.89 (s, 3H), 3.28-3.18 (m, 4H), 2.18-2.02 (m, 4H).

Workup

temperatureto cool to room temperature overnight
filtrationThe yellow solid was filtered off
washwas washed with ethanol

Sources & evidence

ORD record: ord-b3b28b235bca46bd88f4d743f74005f9
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598164B2

Reaction notes

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