Hydrogen Bromide → H-D-Phg-NH2.HBr

HRID 2052264Notes

Reaction equation

HRID 2052264 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@@H:2]([C:9]([NH2:11])=[O:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[BrH:22]>C(O)(=O)C.CCOCC>[NH2:1][C@@H:2]([C:9]([NH2:11])=[O:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[BrH:22]

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 14371254H-D-Phg-NH2

Product 1

HCID 131711684H-D-Phg-NH2.HBrYield 87.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

20.0 g (70 mmoles) of Z-D-Phg-NH2, prepared as described in Step 1, are dissolved in 40 ml of acetic acid, and 70 ml of a 8 n HBr solution in acetic acid are poured to the solution. After 1 hour the reaction mixture is diluted with ether and the hydrobromide is filtered off. The salt, containing a great excess of HBr, is recrystallized from a tenfold amount of ethanol. 14.15 g (87.5%) of H-D-Phg-NH2.HBr are obtained; m.p.: 263.0°-263.5° C. (determined on a Koffler apparatus). Rf8 (HBr): 0.25; Rf8 base: 0.40. [α]D =-75.6° (c=1.0, in dimethyl formamide).

Workup

  1. filtrationthe hydrobromide is filtered off
  2. additionThe salt, containing a great excess of HBr
  3. customis recrystallized from a tenfold amount of ethanol

Sources & evidence

ORD record
ord-2038d3d6b4f94a27b30d79ce9c21f82e
Source dataset
uspto-grants-1980_01
Patent number
US04183909

Reaction notes

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