Hydrochloric Acid → HCID 19911800, compound

HRID 224792Notes

Reaction equation

HRID 224792 reaction equation
[F:1][N:2]([F:20])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11]C(=O)C2C=CC=CC=2)=[CH:7][CH:6]=1.Cl>CO>[F:1][N:2]([F:20])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23330226HCID 23330226, compound

Product 1

HCID 19911800HCID 19911800, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N,N-Difluoro-O-benzoyltyramine (130 mg.) in methanol saturated with HCl was heated at 60° C. for 3 hours. The title compound (40 mg, 40%), isolated by preparative layer chromatography on silica gel, was a liquid at room temperature, and exhibited 1H n.m.r. signals, (CDCl3) at δ 3.0 (2H, t, J=8 Hz, Ar--CH2 --CH2 --), δ 3.6 (2H, tt, JHH =8 Hz, JHF =27 Hz, --CH2CH2NF2), δ 4.9 (1H, bs, exchangeable with D2O, --OH) and δ 6.8 (4H, m, aromatic protons); 19F n.m.r. signals (CDCl3) at φ*-55.3 (t, JHF =27 Hz, --CH2NF2). The mass spectrum had a molecular ion at m/e 173 [Accurate mass: M(173)=173.0653; calc. for C8H9NF2O=173.0652].

Sources & evidence

ORD record
ord-edaf0a18303d4f44b995d448c4264f4f
Source dataset
uspto-grants-1980_11
Patent number
US04234515

Reaction notes

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