Hydrochloric Acid → HCID 86697531, compound

HRID 626839Notes

Reaction equation

HRID 626839 reaction equation
[Cl:1][C:2]1[CH:18]=[C:17]([CH:19]([OH:21])[CH3:20])[C:5]([O:6][CH2:7][CH2:8][NH:9]C(=O)OC(C)(C)C)=[C:4]([CH:22]=O)[C:3]=1[C:24]#[N:25].Cl>O1CCOCC1>[Cl:1][C:2]1[C:3]([C:24]#[N:25])=[C:4]2[CH:22]=[N:9][CH2:8][CH2:7][O:6][C:5]2=[C:17]([CH:19]([OH:21])[CH3:20])[CH:18]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86697530HCID 86697530, compound

Product 1

HCID 86697531HCID 86697531, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

The crude tert-butyl {2-[4-chloro-3-cyano-2-formyl-6-(1-hydroxyethyl)phenoxy]ethyl}carbamate was dissolved in 1,4-dioxane (16 mL) and was added to an ice cooled 4.0 M hydrogen chloride in dioxane (40 mL) solution. After stirring for 1 h, the reaction was concentrated in vacuo to give 7-chloro-9-(1-hydroxyethyl)-2,3-dihydro-1,4-benzoxazepine-6-carbonitrile as an oil. LCMS calculated for C12H12ClN2O2(M+H)+: m/z=251.1; found: 251.0. 1H NMR (300 MHz, DMSO-d6) δ 8.55 (t, J=2.0 Hz, 1H), 7.75 (s, 1H), 5.53 (d, J=4.6 Hz, 1H), 5.05-4.82 (m, 1H), 4.53-4.24 (m, 2H), 4.20-4.04 (m, 2H), 1.26 (d, J=6.4 Hz, 3H).

Workup

  1. concentrationthe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-764878bdb19541e48e248bee109f07d2
Source dataset
uspto-grants-2016_04
Patent number
US09309251B2

Reaction notes

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