Tetrafluoroboric acid → HCID 12472226, compound

HRID 2107080Notes

Reaction equation

HRID 2107080 reaction equation
[F:1][B-:2]([F:5])([F:4])[F:3].[H+].[C:7]([CH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][N:10]1[C:19](=[O:23])[CH:20]([CH3:22])[CH3:21])#[N:8]>C(O)(=O)C>[F:1][B-:2]([F:5])([F:4])[F:3].[NH2:8][C:7]1[O:23][C:19]([CH:20]([CH3:21])[CH3:22])=[N+:10]2[CH:11]=[CH:12][C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:9]=12

Participants

4

Reactant 2

HCID 28118Tetrafluoroboric acidHCID 12472247HCID 12472247, compound

Product 1

HCID 12472226HCID 12472226, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
5 °C

Procedure

An aqueous solution of fluoroboric acid (48% w/v; 33 ml) was added to a stirred solution of 1-cyano-2-isobutyryl-1,2-dihydroisoquinoline (6.78 g; prepared according to the method described by F. D. Popp and A. Soto, J. Chem. Soc., 1963, 1760) in acetic acid (25 ml) at 60° C. The solution was stirred for 15 minutes and then cooled to 5° C. The solid was collected, washed thoroughly with diethyl ether and dried, to give 1-amino-3-isopropyloxazolo[4,3-a]isoquinolinium tetrafluoroborate (8.55 g) in the form of a pale yellow solid, m.p. 181°-183° C. [Elemental analysis: C, 53.0; H, 4.78; N, 8.9%; Calculated: C, 53.5; H, 4.81; N, 8 9%; N.M.R. in CD3CN): 1.44 (6H, d, J=7 Hz), 3.68 (1H, septet, J=7 Hz), 5.90 (2H, broad s), 7.27 (1H, d, J=8 Hz), 7.48-7.72 (4H, m), 7.92 (1H, d, J=8 Hz); Mass spectrum (fast atom bombardment) m/e=227].

Workup

  1. customprepared
  2. customat 60° C
  3. customThe solid was collected
  4. washwashed thoroughly with diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-ab6e987d092a451abbceeff8bcafb946
Source dataset
uspto-grants-1990_06
Patent number
US04933350

Reaction notes

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